From 32f9307862ced8d25c44fd3b0161b60354559cd8 Mon Sep 17 00:00:00 2001
From: Dario Piotrowicz <dario@cloudflare.com>
Date: Fri, 12 Jun 2026 15:37:39 +0100
Subject: [PATCH 1/4] Graduate autoconfig from experimental to stable (#14276)

---
 .changeset/graduate-autoconfig-stable.md      |   9 +
 .../src/__tests__/autoconfig/run.test.ts      |  29 ++-
 .../src/__tests__/deploy/core.test.ts         |  18 +-
 .../src/__tests__/deploy/entry-points.test.ts | 232 +-----------------
 .../src/__tests__/deploy/open-next.test.ts    |  24 +-
 packages/wrangler/src/deploy/autoconfig.ts    |   6 +-
 packages/wrangler/src/deploy/index.ts         |   7 +-
 packages/wrangler/src/metrics/sanitization.ts |   2 +-
 8 files changed, 62 insertions(+), 265 deletions(-)
 create mode 100644 .changeset/graduate-autoconfig-stable.md

diff --git a/.changeset/graduate-autoconfig-stable.md b/.changeset/graduate-autoconfig-stable.md
new file mode 100644
index 0000000000..0f6c26675d
--- /dev/null
+++ b/.changeset/graduate-autoconfig-stable.md
@@ -0,0 +1,9 @@
+---
+"wrangler": minor
+---
+
+Graduate autoconfig from experimental to stable
+
+The `--experimental-autoconfig` and `--x-autoconfig` deploy CLI flags have been replaced with `--autoconfig`.
+
+Note that the `--autoconfig` flag defaults to `true` and that it can be used to disable Wrangler's auto-configuration logic by setting it to `false` via `--autoconfig=false` or `--no-autoconfig`
diff --git a/packages/wrangler/src/__tests__/autoconfig/run.test.ts b/packages/wrangler/src/__tests__/autoconfig/run.test.ts
index 4d5134bfb2..369a4aeeeb 100644
--- a/packages/wrangler/src/__tests__/autoconfig/run.test.ts
+++ b/packages/wrangler/src/__tests__/autoconfig/run.test.ts
@@ -92,21 +92,38 @@ describe("autoconfig (deploy)", () => {
 		clearOutputFilePath();
 	});
 
-	it("should not check for autoconfig when `deploy` is run with `--x-autoconfig=false`", async ({
+	it("should not run autoconfig when `deploy` is run with `--no-autoconfig`", async ({
 		expect,
 	}) => {
 		writeWorkerSource();
 		writeWranglerConfig({ main: "index.js" });
 		const getDetailsSpy = vi.spyOn(details, "getDetailsForAutoConfig");
-		await runDeploy(expect, `--x-autoconfig=false`);
+		const runSpy = vi.spyOn(run, "runAutoConfig");
+
+		await runDeploy(expect, `--no-autoconfig`);
 
 		expect(getDetailsSpy).not.toHaveBeenCalled();
+		expect(runSpy).not.toHaveBeenCalled();
+	});
+
+	it("should not run autoconfig when `deploy` is run with `--autoconfig=false`", async ({
+		expect,
+	}) => {
+		writeWorkerSource();
+		writeWranglerConfig({ main: "index.js" });
+		const getDetailsSpy = vi.spyOn(details, "getDetailsForAutoConfig");
+		const runSpy = vi.spyOn(run, "runAutoConfig");
+
+		await runDeploy(expect, `--autoconfig=false`);
+
+		expect(getDetailsSpy).not.toHaveBeenCalled();
+		expect(runSpy).not.toHaveBeenCalled();
 	});
 
 	it("should check for autoconfig with flag", async ({ expect }) => {
 		const getDetailsSpy = vi.spyOn(details, "getDetailsForAutoConfig");
 
-		await runDeploy(expect, "--x-autoconfig");
+		await runDeploy(expect, "--autoconfig");
 
 		expect(getDetailsSpy).toHaveBeenCalled();
 	});
@@ -128,7 +145,7 @@ describe("autoconfig (deploy)", () => {
 			);
 		const runSpy = vi.spyOn(run, "runAutoConfig");
 
-		await runDeploy(expect, "--x-autoconfig");
+		await runDeploy(expect, "--autoconfig");
 
 		expect(getDetailsSpy).toHaveBeenCalled();
 		expect(runSpy).toHaveBeenCalled();
@@ -149,7 +166,7 @@ describe("autoconfig (deploy)", () => {
 			);
 		const runSpy = vi.spyOn(run, "runAutoConfig");
 
-		await runDeploy(expect, "--x-autoconfig");
+		await runDeploy(expect, "--autoconfig");
 
 		expect(getDetailsSpy).toHaveBeenCalled();
 		expect(runSpy).not.toHaveBeenCalled();
@@ -182,7 +199,7 @@ describe("autoconfig (deploy)", () => {
 		});
 
 		// Should not throw - just return early
-		await runWrangler("deploy --x-autoconfig");
+		await runWrangler("deploy --autoconfig");
 
 		// Should show warning about Pages project
 		expect(std.warn).toContain(
diff --git a/packages/wrangler/src/__tests__/deploy/core.test.ts b/packages/wrangler/src/__tests__/deploy/core.test.ts
index 0f4ea1fd99..a599b7f9c7 100644
--- a/packages/wrangler/src/__tests__/deploy/core.test.ts
+++ b/packages/wrangler/src/__tests__/deploy/core.test.ts
@@ -535,7 +535,7 @@ describe("deploy", () => {
 		`);
 	});
 
-	it("should error helpfully if pages_build_output_dir is set in wrangler.toml when --x-autoconfig=false", async ({
+	it("should error helpfully if pages_build_output_dir is set in wrangler.toml when --no-autoconfig", async ({
 		expect,
 	}) => {
 		writeWranglerConfig({
@@ -543,7 +543,7 @@ describe("deploy", () => {
 			name: "test-name",
 		});
 		await expect(
-			runWrangler("deploy --x-autoconfig=false")
+			runWrangler("deploy --no-autoconfig")
 		).rejects.toThrowErrorMatchingInlineSnapshot(
 			`
 			[Error: It looks like you've run a Workers-specific command in a Pages project.
@@ -552,7 +552,7 @@ describe("deploy", () => {
 		);
 	});
 
-	it("should error helpfully if pages_build_output_dir is set in wrangler.toml and --x-autoconfig is provided", async ({
+	it("should error helpfully if pages_build_output_dir is set in wrangler.toml", async ({
 		expect,
 	}) => {
 		mockConfirm({
@@ -564,13 +564,13 @@ describe("deploy", () => {
 			pages_build_output_dir: "public",
 			name: "test-name",
 		});
-		await expect(runWrangler("deploy --x-autoconfig")).rejects.toThrowError();
+		await expect(runWrangler("deploy")).rejects.toThrowError();
 		expect(std.warn).toContain(
 			"It seems that you have run `wrangler deploy` on a Pages project, `wrangler pages deploy` should be used instead."
 		);
 	});
 
-	it("should attempt to run the autoconfig flow when pages_build_output_dir and (--x-autoconfig is used)", async ({
+	it("should attempt to run the autoconfig flow when pages_build_output_dir", async ({
 		expect,
 	}) => {
 		writeWranglerConfig({
@@ -603,7 +603,7 @@ describe("deploy", () => {
 			result: false,
 		});
 
-		await runWrangler("deploy --x-autoconfig");
+		await runWrangler("deploy");
 
 		expect(getDetailsForAutoConfigSpy).toHaveBeenCalled();
 
@@ -612,7 +612,7 @@ describe("deploy", () => {
 		);
 	});
 
-	it("in non-interactive mode, attempts to deploy a Pages project when --x-autoconfig is used", async ({
+	it("in non-interactive mode, attempts to deploy a Pages project using autoconfig", async ({
 		expect,
 	}) => {
 		setIsTTY(false);
@@ -642,7 +642,7 @@ describe("deploy", () => {
 
 		// The command will fail later due to missing entry-point, but we can still verify
 		// that the deployment of the (Pages) project was attempted
-		await expect(runWrangler("deploy --x-autoconfig")).rejects.toThrow();
+		await expect(runWrangler("deploy")).rejects.toThrow();
 
 		expect(getDetailsForAutoConfigSpy).toHaveBeenCalled();
 
@@ -1433,7 +1433,7 @@ describe("deploy", () => {
 			};
 		});
 
-		await runWrangler("deploy --x-autoconfig --dry-run", {
+		await runWrangler("deploy --dry-run", {
 			...process.env,
 			WRANGLER_OUTPUT_FILE_PATH: outputFile,
 		});
diff --git a/packages/wrangler/src/__tests__/deploy/entry-points.test.ts b/packages/wrangler/src/__tests__/deploy/entry-points.test.ts
index f981ec791d..e0301090de 100644
--- a/packages/wrangler/src/__tests__/deploy/entry-points.test.ts
+++ b/packages/wrangler/src/__tests__/deploy/entry-points.test.ts
@@ -340,7 +340,7 @@ export default{
 			expect(std.err).toMatchInlineSnapshot(`""`);
 		});
 
-		it("should not trigger autoconfig on `wrangler deploy <script>` when called with `--x-autoconfig`", async ({
+		it("should not trigger autoconfig on `wrangler deploy <script>`", async ({
 			expect,
 		}) => {
 			vi.mock(import("../../autoconfig/details"), { spy: true });
@@ -358,7 +358,7 @@ export default{
 			mockUploadWorkerRequest({ expectedEntry: "var foo = 100;" });
 			mockSubDomainRequest();
 
-			await runWrangler("deploy ./src/index.js --x-autoconfig");
+			await runWrangler("deploy ./src/index.js");
 
 			expect(getDetailsForAutoConfigSpy).not.toHaveBeenCalled();
 			expect(runAutoConfigSpy).not.toHaveBeenCalled();
@@ -885,75 +885,7 @@ addEventListener('fetch', event => {});`
 				vi.useRealTimers();
 			});
 
-			// TODO: remove this test once autoconfig goes GA and its experimental opt-in flag is removed
-			it("should handle `wrangler deploy <directory>`", async ({ expect }) => {
-				mockPrompt({
-					text: "What do you want to name your project?",
-					options: { defaultValue: "my-site" },
-					result: "test-name",
-				});
-				mockConfirm({
-					text: "No compatibility date is set. Would you like to use today's date (2024-01-01)?",
-					result: true,
-				});
-				mockConfirm({
-					text: "Do you want Wrangler to write a wrangler.jsonc config file to store this configuration?\nThis will allow you to simply run `wrangler deploy` on future deployments.",
-					result: true,
-				});
-
-				const bodies: AssetManifest[] = [];
-				await mockAUSRequest(bodies);
-
-				await runWrangler("deploy ./assets");
-				expect(bodies.length).toBe(1);
-				expect(bodies[0]).toEqual({
-					manifest: {
-						"/index.html": {
-							hash: "8308ce789f3d08668ce87176838d59d0",
-							size: 17,
-						},
-					},
-				});
-				expect(fs.readFileSync("wrangler.jsonc", "utf-8"))
-					.toMatchInlineSnapshot(`
-						"{
-						  "name": "test-name",
-						  "compatibility_date": "2024-01-01",
-						  "assets": {
-						    "directory": "./assets"
-						  }
-						}"
-					`);
-				expect(std.out).toMatchInlineSnapshot(`
-					"
-					 ⛅️ wrangler x.x.x
-					──────────────────
-
-
-					Wrote
-					{
-					  "name": "test-name",
-					  "compatibility_date": "2024-01-01",
-					  "assets": {
-					    "directory": "./assets"
-					  }
-					}
-					 to <cwd>/wrangler.jsonc.
-
-					Simply run \`wrangler deploy\` next time. Wrangler will automatically use the configuration saved to wrangler.jsonc.
-
-					Proceeding with deployment...
-
-					Total Upload: xx KiB / gzip: xx KiB
-					Worker Startup Time: 100 ms
-					Uploaded test-name (TIMINGS)
-					Deployed test-name triggers (TIMINGS)
-					  https://test-name.test-sub-domain.workers.dev
-					Current Version ID: Galaxy-Class"
-				`);
-			});
-
-			it("should handle interactive `wrangler deploy <directory>` flows without triggering autoconfig when called with `--x-autoconfig`", async ({
+			it("should handle interactive `wrangler deploy <directory>` flows without triggering autoconfig", async ({
 				expect,
 			}) => {
 				vi.mock(import("../../autoconfig/details"), { spy: true });
@@ -983,7 +915,7 @@ addEventListener('fetch', event => {});`
 				const bodies: AssetManifest[] = [];
 				await mockAUSRequest(bodies);
 
-				await runWrangler("deploy ./assets --x-autoconfig");
+				await runWrangler("deploy ./assets");
 				expect(bodies.length).toBe(1);
 				expect(bodies[0]).toEqual({
 					manifest: {
@@ -1034,78 +966,7 @@ addEventListener('fetch', event => {});`
 				expect(runAutoConfigSpy).not.toHaveBeenCalled();
 			});
 
-			// TODO: remove this test once autoconfig goes GA and its experimental opt-in flag is removed
-			it("should handle `wrangler deploy --assets` without name or compat date", async ({
-				expect,
-			}) => {
-				// if the user has used --assets flag and args.script is not set, we just need to prompt for the name and add compat date
-				mockPrompt({
-					text: "What do you want to name your project?",
-					options: { defaultValue: "my-site" },
-					result: "test-name",
-				});
-				mockConfirm({
-					text: "No compatibility date is set. Would you like to use today's date (2024-01-01)?",
-					result: true,
-				});
-				mockConfirm({
-					text: "Do you want Wrangler to write a wrangler.jsonc config file to store this configuration?\nThis will allow you to simply run `wrangler deploy` on future deployments.",
-					result: true,
-				});
-
-				const bodies: AssetManifest[] = [];
-				await mockAUSRequest(bodies);
-
-				await runWrangler("deploy --assets ./assets");
-				expect(bodies.length).toBe(1);
-				expect(bodies[0]).toEqual({
-					manifest: {
-						"/index.html": {
-							hash: "8308ce789f3d08668ce87176838d59d0",
-							size: 17,
-						},
-					},
-				});
-				expect(fs.readFileSync("wrangler.jsonc", "utf-8"))
-					.toMatchInlineSnapshot(`
-						"{
-						  "name": "test-name",
-						  "compatibility_date": "2024-01-01",
-						  "assets": {
-						    "directory": "./assets"
-						  }
-						}"
-					`);
-				expect(std.out).toMatchInlineSnapshot(`
-					"
-					 ⛅️ wrangler x.x.x
-					──────────────────
-
-
-					Wrote
-					{
-					  "name": "test-name",
-					  "compatibility_date": "2024-01-01",
-					  "assets": {
-					    "directory": "./assets"
-					  }
-					}
-					 to <cwd>/wrangler.jsonc.
-
-					Simply run \`wrangler deploy\` next time. Wrangler will automatically use the configuration saved to wrangler.jsonc.
-
-					Proceeding with deployment...
-
-					Total Upload: xx KiB / gzip: xx KiB
-					Worker Startup Time: 100 ms
-					Uploaded test-name (TIMINGS)
-					Deployed test-name triggers (TIMINGS)
-					  https://test-name.test-sub-domain.workers.dev
-					Current Version ID: Galaxy-Class"
-				`);
-			});
-
-			it("should handle `wrangler deploy --assets` without name or compat date without triggering autoconfig when called with `--x-autoconfig`", async ({
+			it("should handle `wrangler deploy --assets` without name or compat date without triggering autoconfig", async ({
 				expect,
 			}) => {
 				vi.mock(import("../../autoconfig/details"), { spy: true });
@@ -1136,88 +997,7 @@ addEventListener('fetch', event => {});`
 				const bodies: AssetManifest[] = [];
 				await mockAUSRequest(bodies);
 
-				await runWrangler("deploy --assets ./assets --x-autoconfig");
-				expect(bodies.length).toBe(1);
-				expect(bodies[0]).toEqual({
-					manifest: {
-						"/index.html": {
-							hash: "8308ce789f3d08668ce87176838d59d0",
-							size: 17,
-						},
-					},
-				});
-				expect(fs.readFileSync("wrangler.jsonc", "utf-8"))
-					.toMatchInlineSnapshot(`
-						"{
-						  "name": "test-name",
-						  "compatibility_date": "2024-01-01",
-						  "assets": {
-						    "directory": "./assets"
-						  }
-						}"
-					`);
-				expect(std.out).toMatchInlineSnapshot(`
-					"
-					 ⛅️ wrangler x.x.x
-					──────────────────
-
-
-					Wrote
-					{
-					  "name": "test-name",
-					  "compatibility_date": "2024-01-01",
-					  "assets": {
-					    "directory": "./assets"
-					  }
-					}
-					 to <cwd>/wrangler.jsonc.
-
-					Simply run \`wrangler deploy\` next time. Wrangler will automatically use the configuration saved to wrangler.jsonc.
-
-					Proceeding with deployment...
-
-					Total Upload: xx KiB / gzip: xx KiB
-					Worker Startup Time: 100 ms
-					Uploaded test-name (TIMINGS)
-					Deployed test-name triggers (TIMINGS)
-					  https://test-name.test-sub-domain.workers.dev
-					Current Version ID: Galaxy-Class"
-				`);
-				expect(getDetailsForAutoConfigSpy).not.toHaveBeenCalled();
-				expect(runAutoConfigSpy).not.toHaveBeenCalled();
-			});
-
-			it("should not trigger autoconfig on `wrangler deploy <directory>` when called with `--x-autoconfig`", async ({
-				expect,
-			}) => {
-				vi.mock(import("../../autoconfig/details"), { spy: true });
-				vi.mock(import("../../autoconfig/run"), { spy: true });
-
-				const getDetailsForAutoConfigSpy = (
-					await import("../../autoconfig/details")
-				).getDetailsForAutoConfig;
-
-				const runAutoConfigSpy = (await import("../../autoconfig/run"))
-					.runAutoConfig;
-
-				mockPrompt({
-					text: "What do you want to name your project?",
-					options: { defaultValue: "my-site" },
-					result: "test-name",
-				});
-				mockConfirm({
-					text: "No compatibility date is set. Would you like to use today's date (2024-01-01)?",
-					result: true,
-				});
-				mockConfirm({
-					text: "Do you want Wrangler to write a wrangler.jsonc config file to store this configuration?\nThis will allow you to simply run `wrangler deploy` on future deployments.",
-					result: true,
-				});
-
-				const bodies: AssetManifest[] = [];
-				await mockAUSRequest(bodies);
-
-				await runWrangler("deploy ./assets --x-autoconfig");
+				await runWrangler("deploy --assets ./assets");
 				expect(bodies.length).toBe(1);
 				expect(bodies[0]).toEqual({
 					manifest: {
diff --git a/packages/wrangler/src/__tests__/deploy/open-next.test.ts b/packages/wrangler/src/__tests__/deploy/open-next.test.ts
index 256c560f5a..3d604692f4 100644
--- a/packages/wrangler/src/__tests__/deploy/open-next.test.ts
+++ b/packages/wrangler/src/__tests__/deploy/open-next.test.ts
@@ -172,7 +172,6 @@ describe("deploy", () => {
 				"npx",
 				"wrangler",
 				"deploy",
-				"--x-autoconfig",
 			]);
 			const runCommandSpy = (
 				await import("@cloudflare/cli-shared-helpers/command")
@@ -180,17 +179,12 @@ describe("deploy", () => {
 
 			await mockOpenNextLikeProject();
 
-			await runWrangler("deploy --x-autoconfig");
+			await runWrangler("deploy");
 
 			expect(runCommandSpy).toHaveBeenCalledOnce();
 			const call = (runCommandSpy as unknown as MockInstance).mock.calls[0];
 			const [command, options] = call;
-			expect(command).toEqual([
-				"npx",
-				"opennextjs-cloudflare",
-				"deploy",
-				"--x-autoconfig",
-			]);
+			expect(command).toEqual(["npx", "opennextjs-cloudflare", "deploy"]);
 			expect(options).toMatchObject({
 				env: {
 					// Note: we want to ensure that OPEN_NEXT_DEPLOY has been set, this is not strictly necessary but it helps us
@@ -221,7 +215,6 @@ describe("deploy", () => {
 				"wrangler",
 				"deploy",
 				"--keep-vars",
-				"--x-autoconfig",
 			]);
 			const runCommandSpy = (
 				await import("@cloudflare/cli-shared-helpers/command")
@@ -229,7 +222,7 @@ describe("deploy", () => {
 
 			await mockOpenNextLikeProject();
 
-			await runWrangler("deploy --x-autoconfig");
+			await runWrangler("deploy");
 
 			expect(runCommandSpy).toHaveBeenCalledOnce();
 			const call = (runCommandSpy as unknown as MockInstance).mock.calls[0];
@@ -241,7 +234,6 @@ describe("deploy", () => {
 				// `opennextjs-cloudflare deploy` accepts all the same arguments `wrangler deploy` does (since it then forwards them
 				// to wrangler), so we do want to make sure that arguments are indeed forwarded to `opennextjs-cloudflare deploy`
 				"--keep-vars",
-				"--x-autoconfig",
 			]);
 			expect(options).toMatchObject({
 				env: {
@@ -276,7 +268,7 @@ describe("deploy", () => {
 
 			await mockOpenNextLikeProject();
 
-			await runWrangler("deploy --x-autoconfig");
+			await runWrangler("deploy");
 
 			expect(runCommandSpy).not.toHaveBeenCalledOnce();
 
@@ -299,7 +291,7 @@ describe("deploy", () => {
 			expect(std.warn).toMatchInlineSnapshot(`""`);
 		});
 
-		it("should not delegate to open-next deploy when --x-autoconfig=false is provided", async ({
+		it("should not delegate to open-next deploy when --no-autoconfig is provided", async ({
 			expect,
 		}) => {
 			const runCommandSpy = (
@@ -308,7 +300,7 @@ describe("deploy", () => {
 
 			await mockOpenNextLikeProject();
 
-			await runWrangler("deploy --x-autoconfig=false");
+			await runWrangler("deploy --no-autoconfig");
 
 			expect(runCommandSpy).not.toHaveBeenCalledOnce();
 
@@ -343,7 +335,7 @@ describe("deploy", () => {
 			// Let's delete the next.config.js file
 			fs.rmSync("./next.config.js");
 
-			await runWrangler("deploy --x-autoconfig");
+			await runWrangler("deploy");
 
 			expect(runCommandSpy).not.toHaveBeenCalledOnce();
 
@@ -378,7 +370,7 @@ describe("deploy", () => {
 			// Let's delete the open-next.config.ts file
 			fs.rmSync("./open-next.config.ts");
 
-			await runWrangler("deploy --x-autoconfig");
+			await runWrangler("deploy --autoconfig");
 
 			expect(runCommandSpy).not.toHaveBeenCalledOnce();
 
diff --git a/packages/wrangler/src/deploy/autoconfig.ts b/packages/wrangler/src/deploy/autoconfig.ts
index 4210082095..13a044f38b 100644
--- a/packages/wrangler/src/deploy/autoconfig.ts
+++ b/packages/wrangler/src/deploy/autoconfig.ts
@@ -55,11 +55,11 @@ type DeployConfigFlags = {
  * The full set of CLI args consumed by the interactive deploy autoconfig flow.
  * Combines the base config/script/name args from {@link ReadConfigCommandArgs},
  * all deployment-affecting flags from {@link DeployConfigFlags}, and the
- * autoconfig-specific control flags (experimentalAutoconfig, assets, dryRun, latest).
+ * autoconfig-specific control flags (autoconfig, assets, dryRun, latest).
  */
 type AutoConfigArgs = ReadConfigCommandArgs &
 	DeployConfigFlags & {
-		experimentalAutoconfig: boolean | undefined;
+		autoconfig: boolean | undefined;
 		path: string | undefined;
 		assets: string | undefined;
 		dryRun: boolean | undefined;
@@ -77,7 +77,7 @@ export async function maybeRunAutoConfig<Args extends AutoConfigArgs>(
 	config: Config
 ): Promise<{ config: Config; aborted: boolean }> {
 	const shouldRunAutoConfig =
-		args.experimentalAutoconfig &&
+		args.autoconfig &&
 		// If there is a positional parameter, an assets directory specified via --assets, or an
 		// explicit --config path then we don't want to run autoconfig since we assume that the
 		// user knows what they are doing and that they are specifying what needs to be deployed
diff --git a/packages/wrangler/src/deploy/index.ts b/packages/wrangler/src/deploy/index.ts
index d9dbb530e4..ea070958ed 100644
--- a/packages/wrangler/src/deploy/index.ts
+++ b/packages/wrangler/src/deploy/index.ts
@@ -91,10 +91,9 @@ export const deployCommand = createCommand({
 			type: "boolean",
 			default: false,
 		},
-		"experimental-autoconfig": {
-			alias: ["x-autoconfig"],
+		autoconfig: {
 			describe:
-				"Experimental: Enables framework detection and automatic configuration when deploying",
+				"Enables framework detection and automatic configuration when deploying",
 			type: "boolean",
 			default: true,
 		},
@@ -127,7 +126,7 @@ export const deployCommand = createCommand({
 		// As a precaution we're gating the feature under the autoconfig flag for the time being.
 		// If the user explicitly provided a --config path, they are targeting a specific Worker config and we should not delegate
 		if (
-			args.experimentalAutoconfig &&
+			args.autoconfig &&
 			!args.config &&
 			!args.dryRun &&
 			(await maybeDelegateToOpenNextDeployCommand(process.cwd()))
diff --git a/packages/wrangler/src/metrics/sanitization.ts b/packages/wrangler/src/metrics/sanitization.ts
index 6f89415e00..12e086b002 100644
--- a/packages/wrangler/src/metrics/sanitization.ts
+++ b/packages/wrangler/src/metrics/sanitization.ts
@@ -83,7 +83,7 @@ export const COMMAND_ARG_ALLOW_LIST: AllowList = {
 		updateConfig: ALLOW,
 		nodeCompat: ALLOW,
 		enableContainers: ALLOW,
-		xAutoconfig: ALLOW,
+		autoconfig: ALLOW,
 		ignoreDefaults: ALLOW,
 	},
 	tail: { status: ALLOW },

From 21dbc1242ed097ce209a24bf61a2dad6e3d46d08 Mon Sep 17 00:00:00 2001
From: Dario Piotrowicz <dario@cloudflare.com>
Date: Fri, 12 Jun 2026 15:49:11 +0100
Subject: [PATCH 2/4] Suggest Cloudflare skills installation after commands
 instead of before (#14264)
MIME-Version: 1.0
Content-Type: text/plain; charset=UTF-8
Content-Transfer-Encoding: 8bit

Co-authored-by: Matt ‘TK’ Taylor <matttaylor@cloudflare.com>
---
 .changeset/suggest-skills-after-commands.md   |   9 +
 .../src/__tests__/agent-memory.test.ts        |   4 +-
 .../__tests__/agents-skills-install.test.ts   | 512 ++++++++++++++++--
 packages/wrangler/src/__tests__/ai.test.ts    |   8 +-
 packages/wrangler/src/__tests__/cert.test.ts  |   2 +-
 .../src/__tests__/cloudchamber/create.test.ts |   2 +-
 .../src/__tests__/cloudchamber/curl.test.ts   |   2 +-
 .../src/__tests__/cloudchamber/delete.test.ts |   2 +-
 .../src/__tests__/cloudchamber/images.test.ts |   6 +-
 .../src/__tests__/cloudchamber/list.test.ts   |   2 +-
 .../src/__tests__/cloudchamber/modify.test.ts |   2 +-
 .../src/__tests__/containers/delete.test.ts   |   2 +-
 .../src/__tests__/containers/images.test.ts   |   4 +-
 .../src/__tests__/containers/info.test.ts     |   2 +-
 .../__tests__/containers/instances.test.ts    |   2 +-
 .../src/__tests__/containers/list.test.ts     |   2 +-
 .../src/__tests__/containers/push.test.ts     |   2 +-
 .../__tests__/containers/registries.test.ts   |   2 +-
 .../src/__tests__/containers/ssh.test.ts      |   2 +-
 packages/wrangler/src/__tests__/d1/d1.test.ts |   8 +-
 .../src/__tests__/deploy/secrets.test.ts      |  90 +--
 .../src/__tests__/deployments.test.ts         |   2 +-
 packages/wrangler/src/__tests__/docs.test.ts  |   2 +-
 .../experimental-commands-api.test.ts         |   2 +-
 .../wrangler/src/__tests__/hyperdrive.test.ts |   4 +-
 packages/wrangler/src/__tests__/index.test.ts |  14 +-
 .../wrangler/src/__tests__/kv/help.test.ts    |   6 +-
 .../wrangler/src/__tests__/kv/key.test.ts     |  18 +-
 .../src/__tests__/kv/namespace.test.ts        |   6 +-
 .../src/__tests__/mtls-certificates.test.ts   |   2 +-
 .../src/__tests__/pages/deploy.test.ts        |   2 +-
 .../src/__tests__/pages/pages.test.ts         |  14 +-
 .../wrangler/src/__tests__/provision.test.ts  |  62 +--
 .../queues/queues-subscription.test.ts        |   8 +-
 .../src/__tests__/queues/queues.test.ts       |  88 +--
 .../wrangler/src/__tests__/r2/bucket.test.ts  |  50 +-
 .../wrangler/src/__tests__/r2/bulk.test.ts    |   2 +-
 .../wrangler/src/__tests__/r2/help.test.ts    |   4 +-
 .../src/__tests__/r2/local-uploads.test.ts    |   2 +-
 .../wrangler/src/__tests__/r2/object.test.ts  |   2 +-
 .../register-yargs-command-skills.test.ts     |  93 +++-
 .../src/__tests__/secrets-store.test.ts       |   4 +-
 packages/wrangler/src/__tests__/setup.test.ts |   2 +-
 .../src/__tests__/tunnel/tunnel.test.ts       |   2 +-
 .../src/__tests__/vectorize/vectorize.test.ts |  10 +-
 .../__tests__/versions/versions.help.test.ts  |   4 +-
 .../wrangler/src/__tests__/vitest.setup.ts    |   5 +-
 packages/wrangler/src/__tests__/vpc.test.ts   |   4 +-
 .../src/__tests__/worker-namespace.test.ts    |  10 +-
 .../wrangler/src/__tests__/workflows.test.ts  |   4 +-
 .../wrangler/src/agents-skills-install.ts     | 125 ++++-
 packages/wrangler/src/build/index.ts          |   1 +
 packages/wrangler/src/check/commands.ts       |   3 +
 packages/wrangler/src/complete.ts             |   1 -
 .../src/core/register-yargs-command.ts        |  31 +-
 packages/wrangler/src/core/types.ts           |  15 +-
 packages/wrangler/src/delete.ts               |   3 +
 packages/wrangler/src/deploy/index.ts         |   1 +
 packages/wrangler/src/docs/index.ts           |   1 +
 packages/wrangler/src/index.ts                |   2 +-
 packages/wrangler/src/init.ts                 |   1 +
 packages/wrangler/src/metrics/commands.ts     |   7 +
 packages/wrangler/src/preview/index.ts        |  18 +
 packages/wrangler/src/secret/index.ts         |   4 +
 packages/wrangler/src/setup.ts                |   3 +
 packages/wrangler/src/triggers/index.ts       |   1 +
 .../wrangler/src/type-generation/index.ts     |   1 +
 packages/wrangler/src/user/commands.ts        |   4 +
 packages/wrangler/src/versions/deploy.ts      |   1 +
 .../wrangler/src/versions/deployments/list.ts |   1 +
 .../src/versions/deployments/status.ts        |   1 +
 .../wrangler/src/versions/deployments/view.ts |   3 +
 packages/wrangler/src/versions/list.ts        |   1 +
 .../wrangler/src/versions/rollback/index.ts   |   3 +
 .../wrangler/src/versions/secrets/bulk.ts     |   1 +
 .../wrangler/src/versions/secrets/delete.ts   |   1 +
 .../wrangler/src/versions/secrets/list.ts     |   1 +
 packages/wrangler/src/versions/secrets/put.ts |   1 +
 packages/wrangler/src/versions/upload.ts      |   1 +
 packages/wrangler/src/versions/view.ts        |   1 +
 80 files changed, 993 insertions(+), 340 deletions(-)
 create mode 100644 .changeset/suggest-skills-after-commands.md

diff --git a/.changeset/suggest-skills-after-commands.md b/.changeset/suggest-skills-after-commands.md
new file mode 100644
index 0000000000..c6a3f529f2
--- /dev/null
+++ b/.changeset/suggest-skills-after-commands.md
@@ -0,0 +1,9 @@
+---
+"wrangler": minor
+---
+
+Suggest Cloudflare skills installation after commands instead of before
+
+The automatic prompt to install Cloudflare skills for detected AI coding agents no longer runs before every Wrangler command. Instead, Wrangler now suggests installing skills, when appropriate, after some commands complete successfully. Commands that output JSON suppress the suggestion to keep their output clean. The `--install-skills` flag remains available on all commands to explicitly run the skills installation flow before the command executes, without prompting.
+
+As before, Wrangler asks the skills installation question at most once. The skills install metadata file is now written before the confirmation prompt is shown, so even if the user interrupts the process (e.g. CTRL+C, closing the terminal) during the prompt, the question is recorded as unanswered and will not reappear on subsequent runs.
diff --git a/packages/wrangler/src/__tests__/agent-memory.test.ts b/packages/wrangler/src/__tests__/agent-memory.test.ts
index 5dca762457..2d73332684 100644
--- a/packages/wrangler/src/__tests__/agent-memory.test.ts
+++ b/packages/wrangler/src/__tests__/agent-memory.test.ts
@@ -44,7 +44,7 @@ describe("agent-memory help", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]"
 		`);
 	});
@@ -73,7 +73,7 @@ describe("agent-memory help", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]"
 		`);
 	});
diff --git a/packages/wrangler/src/__tests__/agents-skills-install.test.ts b/packages/wrangler/src/__tests__/agents-skills-install.test.ts
index f233cb09de..7627ed3e05 100644
--- a/packages/wrangler/src/__tests__/agents-skills-install.test.ts
+++ b/packages/wrangler/src/__tests__/agents-skills-install.test.ts
@@ -6,16 +6,18 @@ import { runInTempDir } from "@cloudflare/workers-utils/test-helpers";
 import { detectAgenticEnvironment } from "am-i-vibing";
 import ci from "ci-info";
 import { http, HttpResponse } from "msw";
+import prompts from "prompts";
 import { afterEach, beforeEach, describe, test, vi } from "vitest";
+import {
+	skillInstallPromptMessageAfterWranglerCommandHandler,
+	type runSkillsInstallFlow as RunFlowFnType,
+	type telemetryCurrentAgentSkillsInstalled as TelemetryFnType,
+} from "../agents-skills-install";
 import { sendMetricsEvent } from "../metrics/send-event";
 import { mockConsoleMethods } from "./helpers/mock-console";
 import { clearDialogs, mockConfirm } from "./helpers/mock-dialogs";
 import { useMockIsTTY } from "./helpers/mock-istty";
 import { msw } from "./helpers/msw";
-import type {
-	maybeInstallCloudflareSkillsGlobally as InstallFnType,
-	telemetryCurrentAgentSkillsInstalled as TelemetryFnType,
-} from "../agents-skills-install";
 import type * as SendEventModule from "../metrics/send-event";
 
 // Undo the global no-op mock from vitest.setup.ts so we test the real implementation
@@ -98,11 +100,13 @@ function readMetadataFile(): Record<string, unknown> {
  * Re-imports the agents-skills-install module with a fresh module graph.
  * This is necessary because tests need a clean module state after mocks
  * are reconfigured per test.
+ *
+ * @returns The `runSkillsInstallFlow` function from a fresh module import.
  */
-async function freshImport(): Promise<typeof InstallFnType> {
+async function freshImport(): Promise<typeof RunFlowFnType> {
 	vi.resetModules();
 	const mod = await import("../agents-skills-install");
-	return mod.maybeInstallCloudflareSkillsGlobally;
+	return mod.runSkillsInstallFlow;
 }
 
 /**
@@ -129,11 +133,15 @@ function createAgentDir(dirName: string): void {
 	mkdirSync(path.join(os.homedir(), dirName), { recursive: true });
 }
 
-describe("maybeInstallCloudflareSkillsGlobally", () => {
+describe("runSkillsInstallFlow with force-install prompt", () => {
 	runInTempDir();
 	const std = mockConsoleMethods();
 	const { setIsTTY } = useMockIsTTY();
 
+	/** The prompt message used by the --install-skills global flag. */
+	const installPromptMessage = (agents: string[]) =>
+		`Wrangler detected the following AI coding agents: ${agents.join(", ")}. Would you like to install Cloudflare skills for them?`;
+
 	beforeEach(() => {
 		setIsTTY(true);
 		mockRosieAgents.mockResolvedValue(DEFAULT_AGENTS);
@@ -149,9 +157,38 @@ describe("maybeInstallCloudflareSkillsGlobally", () => {
 			expect,
 		}) => {
 			writeMetadataFile({ accepted: true, date: "2025-01-01T00:00:00Z" });
-			const maybeInstallCloudflareSkillsGlobally = await freshImport();
+			const runSkillsInstallFlow = await freshImport();
+
+			await runSkillsInstallFlow({
+				force: false,
+				promptMessage: installPromptMessage,
+			});
+
+			expect(mockRosieAgents).not.toHaveBeenCalled();
+			expect(mockRosieInstall).not.toHaveBeenCalled();
+			expect(sendMetricsEvent).not.toHaveBeenCalled();
+		});
+
+		test("skips silently when metadata file has accepted='unanswered' (user interrupted prompt)", async ({
+			expect,
+		}) => {
+			writeMetadataFile({
+				version: 1,
+				accepted: "unanswered",
+				date: "2025-01-01T00:00:00Z",
+				detectedAgents: [
+					{
+						name: "Claude Code",
+						rosie: { id: "claude", globalPath: "/fake/.claude/skills" },
+					},
+				],
+			});
+			const runSkillsInstallFlow = await freshImport();
 
-			await maybeInstallCloudflareSkillsGlobally(false);
+			await runSkillsInstallFlow({
+				force: false,
+				promptMessage: installPromptMessage,
+			});
 
 			expect(mockRosieAgents).not.toHaveBeenCalled();
 			expect(mockRosieInstall).not.toHaveBeenCalled();
@@ -175,9 +212,12 @@ describe("maybeInstallCloudflareSkillsGlobally", () => {
 				],
 				installFailed: false,
 			});
-			const maybeInstallCloudflareSkillsGlobally = await freshImport();
+			const runSkillsInstallFlow = await freshImport();
 
-			await maybeInstallCloudflareSkillsGlobally(false);
+			await runSkillsInstallFlow({
+				force: false,
+				promptMessage: installPromptMessage,
+			});
 
 			expect(mockRosieAgents).not.toHaveBeenCalled();
 			expect(mockRosieInstall).not.toHaveBeenCalled();
@@ -195,14 +235,15 @@ describe("maybeInstallCloudflareSkillsGlobally", () => {
 
 		test("force=true ignores existing metadata file", async ({ expect }) => {
 			writeMetadataFile({ accepted: true, date: "2025-01-01T00:00:00Z" });
-			const maybeInstallCloudflareSkillsGlobally = await freshImport();
+			const runSkillsInstallFlow = await freshImport();
 
-			await maybeInstallCloudflareSkillsGlobally(true);
+			await runSkillsInstallFlow({ force: true });
 
 			expect(mockRosieInstall).toHaveBeenCalledWith("cloudflare/skills", {
 				global: true,
 				agent: ["claude"],
 				lockfile: false,
+				onLog: expect.any(Function),
 			});
 			expect(std.out).toContain(
 				"Successfully installed Cloudflare skills for: Claude Code."
@@ -220,9 +261,12 @@ describe("maybeInstallCloudflareSkillsGlobally", () => {
 					installPath: null,
 				},
 			]);
-			const maybeInstallCloudflareSkillsGlobally = await freshImport();
+			const runSkillsInstallFlow = await freshImport();
 
-			await maybeInstallCloudflareSkillsGlobally(false);
+			await runSkillsInstallFlow({
+				force: false,
+				promptMessage: installPromptMessage,
+			});
 
 			expect(mockRosieInstall).not.toHaveBeenCalled();
 			expect(sendMetricsEvent).toHaveBeenCalledWith(
@@ -236,9 +280,12 @@ describe("maybeInstallCloudflareSkillsGlobally", () => {
 			expect,
 		}) => {
 			mockRosieAgents.mockResolvedValueOnce([]);
-			const maybeInstallCloudflareSkillsGlobally = await freshImport();
+			const runSkillsInstallFlow = await freshImport();
 
-			await maybeInstallCloudflareSkillsGlobally(false);
+			await runSkillsInstallFlow({
+				force: false,
+				promptMessage: installPromptMessage,
+			});
 
 			expect(mockRosieInstall).not.toHaveBeenCalled();
 			expect(sendMetricsEvent).toHaveBeenCalledWith(
@@ -252,10 +299,10 @@ describe("maybeInstallCloudflareSkillsGlobally", () => {
 			expect,
 		}) => {
 			mockRosieInstall.mockRejectedValueOnce(new Error("network failure"));
-			const maybeInstallCloudflareSkillsGlobally = await freshImport();
+			const runSkillsInstallFlow = await freshImport();
 
 			// force=true so we don't need to mock the confirm dialog
-			await maybeInstallCloudflareSkillsGlobally(true);
+			await runSkillsInstallFlow({ force: true });
 
 			expect(std.warn).toContain(
 				"Failed to install Cloudflare skills: network failure"
@@ -274,9 +321,12 @@ describe("maybeInstallCloudflareSkillsGlobally", () => {
 			expect,
 		}) => {
 			mockRosieAgents.mockRejectedValueOnce(new Error("WASM load failed"));
-			const maybeInstallCloudflareSkillsGlobally = await freshImport();
+			const runSkillsInstallFlow = await freshImport();
 
-			await maybeInstallCloudflareSkillsGlobally(false);
+			await runSkillsInstallFlow({
+				force: false,
+				promptMessage: installPromptMessage,
+			});
 
 			expect(mockRosieInstall).not.toHaveBeenCalled();
 			expect(sendMetricsEvent).toHaveBeenCalledWith(
@@ -293,9 +343,12 @@ describe("maybeInstallCloudflareSkillsGlobally", () => {
 			expect,
 		}) => {
 			vi.mocked(ci).isCI = true;
-			const maybeInstallCloudflareSkillsGlobally = await freshImport();
+			const runSkillsInstallFlow = await freshImport();
 
-			await maybeInstallCloudflareSkillsGlobally(false);
+			await runSkillsInstallFlow({
+				force: false,
+				promptMessage: installPromptMessage,
+			});
 
 			// Verify neither agent detection nor install was attempted
 			expect(mockRosieAgents).not.toHaveBeenCalled();
@@ -311,14 +364,15 @@ describe("maybeInstallCloudflareSkillsGlobally", () => {
 			expect,
 		}) => {
 			vi.mocked(ci).isCI = true;
-			const maybeInstallCloudflareSkillsGlobally = await freshImport();
+			const runSkillsInstallFlow = await freshImport();
 
-			await maybeInstallCloudflareSkillsGlobally(true);
+			await runSkillsInstallFlow({ force: true });
 
 			expect(mockRosieInstall).toHaveBeenCalledWith("cloudflare/skills", {
 				global: true,
 				agent: ["claude"],
 				lockfile: false,
+				onLog: expect.any(Function),
 			});
 		});
 
@@ -326,9 +380,12 @@ describe("maybeInstallCloudflareSkillsGlobally", () => {
 			expect,
 		}) => {
 			setIsTTY(false);
-			const maybeInstallCloudflareSkillsGlobally = await freshImport();
+			const runSkillsInstallFlow = await freshImport();
 
-			await maybeInstallCloudflareSkillsGlobally(false);
+			await runSkillsInstallFlow({
+				force: false,
+				promptMessage: installPromptMessage,
+			});
 
 			// Nothing has been logged
 			expect(std.out).toEqual("");
@@ -351,9 +408,12 @@ describe("maybeInstallCloudflareSkillsGlobally", () => {
 				text: expect.stringContaining("Claude Code") as unknown as string,
 				result: false,
 			});
-			const maybeInstallCloudflareSkillsGlobally = await freshImport();
+			const runSkillsInstallFlow = await freshImport();
 
-			await maybeInstallCloudflareSkillsGlobally(false);
+			await runSkillsInstallFlow({
+				force: false,
+				promptMessage: installPromptMessage,
+			});
 
 			// must not log a success message when the user declined
 			expect(std.out).not.toContain(
@@ -381,14 +441,18 @@ describe("maybeInstallCloudflareSkillsGlobally", () => {
 				text: expect.stringContaining("Claude Code") as unknown as string,
 				result: true,
 			});
-			const maybeInstallCloudflareSkillsGlobally = await freshImport();
+			const runSkillsInstallFlow = await freshImport();
 
-			await maybeInstallCloudflareSkillsGlobally(false);
+			await runSkillsInstallFlow({
+				force: false,
+				promptMessage: installPromptMessage,
+			});
 
 			expect(mockRosieInstall).toHaveBeenCalledWith("cloudflare/skills", {
 				global: true,
 				agent: ["claude"],
 				lockfile: false,
+				onLog: expect.any(Function),
 			});
 
 			expect(std.out).toContain(
@@ -412,22 +476,126 @@ describe("maybeInstallCloudflareSkillsGlobally", () => {
 			);
 		});
 
+		test("writes metadata with accepted='unanswered' before showing the confirm prompt", async ({
+			expect,
+		}) => {
+			// Intercept the prompts call to inspect the metadata file state at
+			// the moment the confirmation prompt is displayed to the user.
+			vi.mocked(prompts).mockImplementationOnce(() => {
+				const metadata = readMetadataFile();
+				expect(metadata.accepted).toBe("unanswered");
+				expect(metadata.detectedAgents).toEqual([
+					{
+						name: "Claude Code",
+						rosie: { id: "claude", globalPath: "/fake/.claude/skills" },
+					},
+				]);
+				return Promise.resolve({ value: true });
+			});
+			const runSkillsInstallFlow = await freshImport();
+
+			await runSkillsInstallFlow({
+				force: false,
+				promptMessage: installPromptMessage,
+			});
+
+			// After the flow completes, the final metadata should reflect the
+			// user's actual answer, overwriting the "unanswered" marker.
+			const finalMetadata = readMetadataFile();
+			expect(finalMetadata.accepted).toBe(true);
+		});
+
 		test("force=true installs skills without prompting", async ({ expect }) => {
 			// No mockConfirm — if a prompt fires, the test will fail with "Unexpected call to prompts"
-			const maybeInstallCloudflareSkillsGlobally = await freshImport();
+			const runSkillsInstallFlow = await freshImport();
 
-			await maybeInstallCloudflareSkillsGlobally(true);
+			await runSkillsInstallFlow({ force: true });
 
 			expect(mockRosieInstall).toHaveBeenCalledWith("cloudflare/skills", {
 				global: true,
 				agent: ["claude"],
 				lockfile: false,
+				onLog: expect.any(Function),
 			});
 
 			expect(std.out).toContain(
 				"Successfully installed Cloudflare skills for: Claude Code."
 			);
 		});
+
+		test("force=true does not write 'unanswered' metadata before installing", async ({
+			expect,
+		}) => {
+			const runSkillsInstallFlow = await freshImport();
+
+			await runSkillsInstallFlow({ force: true });
+
+			// The final metadata should be accepted=true, never "unanswered"
+			const metadata = readMetadataFile();
+			expect(metadata.accepted).toBe(true);
+		});
+	});
+
+	describe("telemetry command property", () => {
+		test("includes command in skills_install_completed when provided", async ({
+			expect,
+		}) => {
+			const runSkillsInstallFlow = await freshImport();
+
+			await runSkillsInstallFlow({ force: true, command: "deploy" });
+
+			expect(sendMetricsEvent).toHaveBeenCalledWith(
+				"skills_install_completed",
+				{
+					agents: [
+						{
+							name: "Claude Code",
+							rosie: {
+								id: "claude",
+								globalPath: "/fake/.claude/skills",
+							},
+						},
+					],
+					command: "deploy",
+				},
+				{}
+			);
+		});
+
+		test("includes command in skills_install_skipped when provided", async ({
+			expect,
+		}) => {
+			mockRosieAgents.mockResolvedValueOnce([]);
+			const runSkillsInstallFlow = await freshImport();
+
+			await runSkillsInstallFlow({
+				force: false,
+				command: "dev",
+				promptMessage: installPromptMessage,
+			});
+
+			expect(sendMetricsEvent).toHaveBeenCalledWith(
+				"skills_install_skipped",
+				{ reason: "No supported agents detected", command: "dev" },
+				{}
+			);
+		});
+
+		test("omits command from metrics when not provided", async ({ expect }) => {
+			mockRosieAgents.mockResolvedValueOnce([]);
+			const runSkillsInstallFlow = await freshImport();
+
+			await runSkillsInstallFlow({
+				force: false,
+				promptMessage: installPromptMessage,
+			});
+
+			expect(sendMetricsEvent).toHaveBeenCalledWith(
+				"skills_install_skipped",
+				{ reason: "No supported agents detected" },
+				{}
+			);
+		});
 	});
 
 	describe("multiple agents", () => {
@@ -452,14 +620,18 @@ describe("maybeInstallCloudflareSkillsGlobally", () => {
 				text: expect.stringContaining("Claude Code") as unknown as string,
 				result: true,
 			});
-			const maybeInstallCloudflareSkillsGlobally = await freshImport();
+			const runSkillsInstallFlow = await freshImport();
 
-			await maybeInstallCloudflareSkillsGlobally(false);
+			await runSkillsInstallFlow({
+				force: false,
+				promptMessage: installPromptMessage,
+			});
 
 			expect(mockRosieInstall).toHaveBeenCalledWith("cloudflare/skills", {
 				global: true,
 				agent: ["claude", "cursor"],
 				lockfile: false,
+				onLog: expect.any(Function),
 			});
 
 			expect(std.out).toContain(
@@ -475,9 +647,9 @@ describe("maybeInstallCloudflareSkillsGlobally", () => {
 			mockRosieInstall.mockRejectedValueOnce(
 				new Error("tarball download failed")
 			);
-			const maybeInstallCloudflareSkillsGlobally = await freshImport();
+			const runSkillsInstallFlow = await freshImport();
 
-			await maybeInstallCloudflareSkillsGlobally(true);
+			await runSkillsInstallFlow({ force: true });
 
 			expect(std.warn).toContain(
 				"Failed to install Cloudflare skills: tarball download failed"
@@ -519,9 +691,9 @@ describe("maybeInstallCloudflareSkillsGlobally", () => {
 				failedAgents: ["cursor"],
 				installedInstruction: null,
 			});
-			const maybeInstallCloudflareSkillsGlobally = await freshImport();
+			const runSkillsInstallFlow = await freshImport();
 
-			await maybeInstallCloudflareSkillsGlobally(true);
+			await runSkillsInstallFlow({ force: true });
 
 			// Success message should only mention succeeded agents
 			expect(std.out).toContain(
@@ -547,9 +719,12 @@ describe("maybeInstallCloudflareSkillsGlobally", () => {
 				text: expect.stringContaining("Claude Code") as unknown as string,
 				result: true,
 			});
-			const maybeInstallCloudflareSkillsGlobally = await freshImport();
+			const runSkillsInstallFlow = await freshImport();
 
-			await maybeInstallCloudflareSkillsGlobally(false);
+			await runSkillsInstallFlow({
+				force: false,
+				promptMessage: installPromptMessage,
+			});
 
 			const metadata = readMetadataFile();
 			expect(metadata.accepted).toBe(true);
@@ -570,9 +745,12 @@ describe("maybeInstallCloudflareSkillsGlobally", () => {
 				text: expect.stringContaining("Claude Code") as unknown as string,
 				result: false,
 			});
-			const maybeInstallCloudflareSkillsGlobally = await freshImport();
+			const runSkillsInstallFlow = await freshImport();
 
-			await maybeInstallCloudflareSkillsGlobally(false);
+			await runSkillsInstallFlow({
+				force: false,
+				promptMessage: installPromptMessage,
+			});
 
 			const metadata = readMetadataFile();
 			expect(metadata.accepted).toBe(false);
@@ -585,9 +763,12 @@ describe("maybeInstallCloudflareSkillsGlobally", () => {
 				text: expect.stringContaining("Claude Code") as unknown as string,
 				result: false,
 			});
-			const maybeInstallCloudflareSkillsGlobally = await freshImport();
+			const runSkillsInstallFlow = await freshImport();
 
-			await maybeInstallCloudflareSkillsGlobally(false);
+			await runSkillsInstallFlow({
+				force: false,
+				promptMessage: installPromptMessage,
+			});
 
 			const metadata = readMetadataFile();
 			expect(metadata.installFailed).toBeUndefined();
@@ -597,9 +778,9 @@ describe("maybeInstallCloudflareSkillsGlobally", () => {
 			expect,
 		}) => {
 			mockRosieInstall.mockRejectedValueOnce(new Error("download failed"));
-			const maybeInstallCloudflareSkillsGlobally = await freshImport();
+			const runSkillsInstallFlow = await freshImport();
 
-			await maybeInstallCloudflareSkillsGlobally(true);
+			await runSkillsInstallFlow({ force: true });
 
 			const metadata = readMetadataFile();
 			expect(metadata.installFailed).toBe(true);
@@ -621,9 +802,9 @@ describe("maybeInstallCloudflareSkillsGlobally", () => {
 				failedAgents: ["cursor"],
 				installedInstruction: null,
 			});
-			const maybeInstallCloudflareSkillsGlobally = await freshImport();
+			const runSkillsInstallFlow = await freshImport();
 
-			await maybeInstallCloudflareSkillsGlobally(true);
+			await runSkillsInstallFlow({ force: true });
 
 			const metadata = readMetadataFile();
 			expect(metadata.accepted).toBe(true);
@@ -633,14 +814,209 @@ describe("maybeInstallCloudflareSkillsGlobally", () => {
 		test("sets installFailed to false when all agents succeed", async ({
 			expect,
 		}) => {
-			const maybeInstallCloudflareSkillsGlobally = await freshImport();
+			const runSkillsInstallFlow = await freshImport();
+
+			await runSkillsInstallFlow({ force: true });
+
+			const metadata = readMetadataFile();
+			expect(metadata.accepted).toBe(true);
+			expect(metadata.installFailed).toBe(false);
+		});
+	});
+});
+
+describe("runSkillsInstallFlow with custom prompt message", () => {
+	runInTempDir();
+	const std = mockConsoleMethods();
+	const { setIsTTY } = useMockIsTTY();
+
+	beforeEach(() => {
+		setIsTTY(true);
+		mockRosieAgents.mockResolvedValue(DEFAULT_AGENTS);
+		mockRosieInstall.mockResolvedValue(DEFAULT_INSTALL_RESULT);
+	});
+
+	afterEach(() => {
+		clearDialogs();
+	});
+
+	describe("skip conditions", () => {
+		test("skips silently when metadata file exists", async ({ expect }) => {
+			writeMetadataFile({ accepted: true, date: "2025-01-01T00:00:00Z" });
+			const flow = await freshImport();
+
+			await flow({
+				force: false,
+				promptMessage: skillInstallPromptMessageAfterWranglerCommandHandler,
+			});
+
+			expect(mockRosieAgents).not.toHaveBeenCalled();
+			expect(mockRosieInstall).not.toHaveBeenCalled();
+			expect(sendMetricsEvent).not.toHaveBeenCalled();
+		});
+
+		test("skips silently when metadata file records a decline", async ({
+			expect,
+		}) => {
+			writeMetadataFile({ accepted: false, date: "2025-01-01T00:00:00Z" });
+			const flow = await freshImport();
+
+			await flow({
+				force: false,
+				promptMessage: skillInstallPromptMessageAfterWranglerCommandHandler,
+			});
+
+			expect(mockRosieAgents).not.toHaveBeenCalled();
+			expect(mockRosieInstall).not.toHaveBeenCalled();
+			expect(sendMetricsEvent).not.toHaveBeenCalled();
+		});
+
+		test("skips silently when metadata file has accepted='unanswered'", async ({
+			expect,
+		}) => {
+			writeMetadataFile({
+				version: 1,
+				accepted: "unanswered",
+				date: "2025-01-01T00:00:00Z",
+			});
+			const flow = await freshImport();
+
+			await flow({
+				force: false,
+				promptMessage: skillInstallPromptMessageAfterWranglerCommandHandler,
+			});
+
+			expect(mockRosieAgents).not.toHaveBeenCalled();
+			expect(mockRosieInstall).not.toHaveBeenCalled();
+			expect(sendMetricsEvent).not.toHaveBeenCalled();
+		});
 
-			await maybeInstallCloudflareSkillsGlobally(true);
+		test("skips in CI", async ({ expect }) => {
+			vi.mocked(ci).isCI = true;
+			const flow = await freshImport();
+
+			await flow({
+				force: false,
+				promptMessage: skillInstallPromptMessageAfterWranglerCommandHandler,
+			});
+
+			expect(mockRosieInstall).not.toHaveBeenCalled();
+			expect(sendMetricsEvent).toHaveBeenCalledWith(
+				"skills_install_skipped",
+				{ reason: "Running in CI" },
+				{}
+			);
+		});
+
+		test("skips in non-interactive terminal", async ({ expect }) => {
+			setIsTTY(false);
+			const flow = await freshImport();
+
+			await flow({
+				force: false,
+				promptMessage: skillInstallPromptMessageAfterWranglerCommandHandler,
+			});
+
+			expect(std.out).toEqual("");
+			expect(mockRosieInstall).not.toHaveBeenCalled();
+			expect(sendMetricsEvent).toHaveBeenCalledWith(
+				"skills_install_skipped",
+				{ reason: "Non-interactive terminal" },
+				{}
+			);
+		});
+
+		test("skips when no agents are detected", async ({ expect }) => {
+			mockRosieAgents.mockResolvedValueOnce([]);
+			const flow = await freshImport();
+
+			await flow({
+				force: false,
+				promptMessage: skillInstallPromptMessageAfterWranglerCommandHandler,
+			});
+
+			expect(mockRosieInstall).not.toHaveBeenCalled();
+			expect(sendMetricsEvent).toHaveBeenCalledWith(
+				"skills_install_skipped",
+				{ reason: "No supported agents detected" },
+				{}
+			);
+		});
+	});
+
+	describe("prompt message", () => {
+		test("uses the caller-provided prompt message", async ({ expect }) => {
+			mockConfirm({
+				text: "Before you go, Wrangler detected AI coding agents that may not be best configured to work with Cloudflare: Claude Code. Would you like Wrangler to automatically install Cloudflare skills for the best experience?",
+				result: false,
+			});
+			const flow = await freshImport();
+
+			await flow({
+				force: false,
+				promptMessage: skillInstallPromptMessageAfterWranglerCommandHandler,
+			});
+
+			expect(sendMetricsEvent).toHaveBeenCalledWith(
+				"skills_install_skipped",
+				{ reason: "User declined" },
+				{}
+			);
+		});
+	});
+
+	describe("user prompt interaction", () => {
+		test("installs skills when user accepts", async ({ expect }) => {
+			mockConfirm({
+				text: expect.stringContaining(
+					"Would you like Wrangler to automatically install Cloudflare skills"
+				) as unknown as string,
+				result: true,
+			});
+			const flow = await freshImport();
+
+			await flow({
+				force: false,
+				promptMessage: skillInstallPromptMessageAfterWranglerCommandHandler,
+			});
+
+			expect(mockRosieInstall).toHaveBeenCalledWith("cloudflare/skills", {
+				global: true,
+				agent: ["claude"],
+				lockfile: false,
+				onLog: expect.any(Function),
+			});
+
+			expect(std.out).toContain(
+				"Successfully installed Cloudflare skills for: Claude Code."
+			);
 
 			const metadata = readMetadataFile();
 			expect(metadata.accepted).toBe(true);
 			expect(metadata.installFailed).toBe(false);
 		});
+
+		test("writes metadata with accepted=false when user declines", async ({
+			expect,
+		}) => {
+			mockConfirm({
+				text: expect.stringContaining(
+					"Would you like Wrangler to automatically install Cloudflare skills"
+				) as unknown as string,
+				result: false,
+			});
+			const flow = await freshImport();
+
+			await flow({
+				force: false,
+				promptMessage: skillInstallPromptMessageAfterWranglerCommandHandler,
+			});
+
+			expect(mockRosieInstall).not.toHaveBeenCalled();
+
+			const metadata = readMetadataFile();
+			expect(metadata.accepted).toBe(false);
+		});
 	});
 });
 
@@ -922,6 +1298,40 @@ describe("telemetryCurrentAgentSkillsInstalled", () => {
 		expect(result).toBe("manual");
 	});
 
+	test("resolves to 'manual' when metadata has accepted='unanswered' (user interrupted prompt)", async ({
+		expect,
+	}) => {
+		vi.mocked(detectAgenticEnvironment).mockReturnValue({
+			isAgentic: true,
+			id: "claude-code",
+			name: "Claude Code",
+			type: "agent",
+		});
+		createAgentDir(".claude");
+		const claudeSkills = path.join(os.homedir(), ".claude", "skills");
+		mkdirSync(path.join(claudeSkills, "cloudflare"), { recursive: true });
+		const claudeGlobalSkillsPath = path.join(os.homedir(), ".claude", "skills");
+		writeMetadataFile({
+			version: 1,
+			accepted: "unanswered",
+			date: new Date().toISOString(),
+			detectedAgents: [
+				{
+					name: "Claude Code",
+					rosie: { id: "claude", globalPath: claudeGlobalSkillsPath },
+				},
+			],
+		});
+		mockGitHubSkillsApi(["cloudflare", "wrangler"]);
+		const telemetryCurrentAgentSkillsInstalled = await freshTelemetryImport();
+
+		const result = await telemetryCurrentAgentSkillsInstalled();
+
+		// "unanswered" must not be treated as "accepted" — skills were never
+		// installed by Wrangler, so the correct status is "manual".
+		expect(result).toBe("manual");
+	});
+
 	test("uses cached GitHub API response within TTL", async ({ expect }) => {
 		vi.mocked(detectAgenticEnvironment).mockReturnValue({
 			isAgentic: true,
diff --git a/packages/wrangler/src/__tests__/ai.test.ts b/packages/wrangler/src/__tests__/ai.test.ts
index dabc64d70b..febc9ab929 100644
--- a/packages/wrangler/src/__tests__/ai.test.ts
+++ b/packages/wrangler/src/__tests__/ai.test.ts
@@ -32,7 +32,7 @@ describe("ai help", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]"
 		`);
 	});
@@ -65,7 +65,7 @@ describe("ai help", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]"
 		`);
 	});
@@ -89,7 +89,7 @@ describe("ai help", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]"
 		`);
 	});
@@ -112,7 +112,7 @@ describe("ai help", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]"
 		`);
 	});
diff --git a/packages/wrangler/src/__tests__/cert.test.ts b/packages/wrangler/src/__tests__/cert.test.ts
index cc599b0c7c..292f3cafc8 100644
--- a/packages/wrangler/src/__tests__/cert.test.ts
+++ b/packages/wrangler/src/__tests__/cert.test.ts
@@ -506,7 +506,7 @@ describe("wrangler", () => {
 						  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 						      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 						  -h, --help            Show help  [boolean]
-						      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+						      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 						  -v, --version         Show version number  [boolean]"
 					`);
 				});
diff --git a/packages/wrangler/src/__tests__/cloudchamber/create.test.ts b/packages/wrangler/src/__tests__/cloudchamber/create.test.ts
index 4ac66c5ae5..1a2869d85c 100644
--- a/packages/wrangler/src/__tests__/cloudchamber/create.test.ts
+++ b/packages/wrangler/src/__tests__/cloudchamber/create.test.ts
@@ -86,7 +86,7 @@ describe("cloudchamber create", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]
 
 			OPTIONS
diff --git a/packages/wrangler/src/__tests__/cloudchamber/curl.test.ts b/packages/wrangler/src/__tests__/cloudchamber/curl.test.ts
index a4372a58c9..afe443c07b 100644
--- a/packages/wrangler/src/__tests__/cloudchamber/curl.test.ts
+++ b/packages/wrangler/src/__tests__/cloudchamber/curl.test.ts
@@ -43,7 +43,7 @@ describe("cloudchamber curl", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]
 
 			OPTIONS
diff --git a/packages/wrangler/src/__tests__/cloudchamber/delete.test.ts b/packages/wrangler/src/__tests__/cloudchamber/delete.test.ts
index 2b52b86a4f..07e89f24c2 100644
--- a/packages/wrangler/src/__tests__/cloudchamber/delete.test.ts
+++ b/packages/wrangler/src/__tests__/cloudchamber/delete.test.ts
@@ -39,7 +39,7 @@ describe("cloudchamber delete", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]"
 		`);
 	});
diff --git a/packages/wrangler/src/__tests__/cloudchamber/images.test.ts b/packages/wrangler/src/__tests__/cloudchamber/images.test.ts
index 9f7b8a5ec5..9b70aa1bbc 100644
--- a/packages/wrangler/src/__tests__/cloudchamber/images.test.ts
+++ b/packages/wrangler/src/__tests__/cloudchamber/images.test.ts
@@ -41,7 +41,7 @@ describe("cloudchamber image", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]"
 		`);
 	});
@@ -194,7 +194,7 @@ describe("cloudchamber image list", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]
 
 			OPTIONS
@@ -453,7 +453,7 @@ describe("cloudchamber image delete", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]"
 		`);
 	});
diff --git a/packages/wrangler/src/__tests__/cloudchamber/list.test.ts b/packages/wrangler/src/__tests__/cloudchamber/list.test.ts
index 2a3af29565..60f9b89687 100644
--- a/packages/wrangler/src/__tests__/cloudchamber/list.test.ts
+++ b/packages/wrangler/src/__tests__/cloudchamber/list.test.ts
@@ -39,7 +39,7 @@ describe("cloudchamber list", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]
 
 			OPTIONS
diff --git a/packages/wrangler/src/__tests__/cloudchamber/modify.test.ts b/packages/wrangler/src/__tests__/cloudchamber/modify.test.ts
index 4eb5d9e33b..ef93b78d15 100644
--- a/packages/wrangler/src/__tests__/cloudchamber/modify.test.ts
+++ b/packages/wrangler/src/__tests__/cloudchamber/modify.test.ts
@@ -54,7 +54,7 @@ describe("cloudchamber modify", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]
 
 			OPTIONS
diff --git a/packages/wrangler/src/__tests__/containers/delete.test.ts b/packages/wrangler/src/__tests__/containers/delete.test.ts
index 54a79c1373..2a3e043d38 100644
--- a/packages/wrangler/src/__tests__/containers/delete.test.ts
+++ b/packages/wrangler/src/__tests__/containers/delete.test.ts
@@ -40,7 +40,7 @@ describe("containers delete", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]"
 		`);
 	});
diff --git a/packages/wrangler/src/__tests__/containers/images.test.ts b/packages/wrangler/src/__tests__/containers/images.test.ts
index ef4abc9ed7..ec7f89ac05 100644
--- a/packages/wrangler/src/__tests__/containers/images.test.ts
+++ b/packages/wrangler/src/__tests__/containers/images.test.ts
@@ -47,7 +47,7 @@ describe("containers images list", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]
 
 			OPTIONS
@@ -220,7 +220,7 @@ describe("containers images delete", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]
 
 			OPTIONS
diff --git a/packages/wrangler/src/__tests__/containers/info.test.ts b/packages/wrangler/src/__tests__/containers/info.test.ts
index c2fccf56a1..78131f9a44 100644
--- a/packages/wrangler/src/__tests__/containers/info.test.ts
+++ b/packages/wrangler/src/__tests__/containers/info.test.ts
@@ -39,7 +39,7 @@ describe("containers info", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]"
 		`);
 	});
diff --git a/packages/wrangler/src/__tests__/containers/instances.test.ts b/packages/wrangler/src/__tests__/containers/instances.test.ts
index 0cb5a7cfcc..1fc917aac5 100644
--- a/packages/wrangler/src/__tests__/containers/instances.test.ts
+++ b/packages/wrangler/src/__tests__/containers/instances.test.ts
@@ -111,7 +111,7 @@ describe("containers instances", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]
 
 			OPTIONS
diff --git a/packages/wrangler/src/__tests__/containers/list.test.ts b/packages/wrangler/src/__tests__/containers/list.test.ts
index 6b1e8cbfc7..d5a777e622 100644
--- a/packages/wrangler/src/__tests__/containers/list.test.ts
+++ b/packages/wrangler/src/__tests__/containers/list.test.ts
@@ -53,7 +53,7 @@ describe("containers list", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]
 
 			OPTIONS
diff --git a/packages/wrangler/src/__tests__/containers/push.test.ts b/packages/wrangler/src/__tests__/containers/push.test.ts
index 8ebcf9e7d6..dd71749479 100644
--- a/packages/wrangler/src/__tests__/containers/push.test.ts
+++ b/packages/wrangler/src/__tests__/containers/push.test.ts
@@ -50,7 +50,7 @@ describe("containers push", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]
 
 			OPTIONS
diff --git a/packages/wrangler/src/__tests__/containers/registries.test.ts b/packages/wrangler/src/__tests__/containers/registries.test.ts
index 8059656617..a9999887f6 100644
--- a/packages/wrangler/src/__tests__/containers/registries.test.ts
+++ b/packages/wrangler/src/__tests__/containers/registries.test.ts
@@ -40,7 +40,7 @@ describe("containers registries --help", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]"
 		`);
 	});
diff --git a/packages/wrangler/src/__tests__/containers/ssh.test.ts b/packages/wrangler/src/__tests__/containers/ssh.test.ts
index 6bd34615c6..5b95c584fe 100644
--- a/packages/wrangler/src/__tests__/containers/ssh.test.ts
+++ b/packages/wrangler/src/__tests__/containers/ssh.test.ts
@@ -79,7 +79,7 @@ describe("containers ssh", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]
 
 			OPTIONS
diff --git a/packages/wrangler/src/__tests__/d1/d1.test.ts b/packages/wrangler/src/__tests__/d1/d1.test.ts
index 601fac3c4f..981f5c42a4 100644
--- a/packages/wrangler/src/__tests__/d1/d1.test.ts
+++ b/packages/wrangler/src/__tests__/d1/d1.test.ts
@@ -34,7 +34,7 @@ describe("d1", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]"
 		`);
 	});
@@ -74,7 +74,7 @@ describe("d1", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]"
 		`);
 	});
@@ -101,7 +101,7 @@ describe("d1", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]"
 		`);
 	});
@@ -126,7 +126,7 @@ describe("d1", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]"
 		`);
 	});
diff --git a/packages/wrangler/src/__tests__/deploy/secrets.test.ts b/packages/wrangler/src/__tests__/deploy/secrets.test.ts
index bb469b6d3f..5a2806f4dc 100644
--- a/packages/wrangler/src/__tests__/deploy/secrets.test.ts
+++ b/packages/wrangler/src/__tests__/deploy/secrets.test.ts
@@ -133,21 +133,21 @@ describe("deploy secrets", () => {
 			await runWrangler(`deploy --secrets-file ${secretsFile}`);
 
 			expect(std.out).toMatchInlineSnapshot(`
-			"
-			 ⛅️ wrangler x.x.x
-			──────────────────
-			Total Upload: xx KiB / gzip: xx KiB
-			Worker Startup Time: 100 ms
-			Your Worker has access to the following bindings:
-			Binding                       Resource
-			env.SECRET1 ("(hidden)")      Environment Variable
-			env.SECRET2 ("(hidden)")      Environment Variable
-
-			Uploaded test-name (TIMINGS)
-			Deployed test-name triggers (TIMINGS)
-			  https://test-name.test-sub-domain.workers.dev
-			Current Version ID: Galaxy-Class"
-		`);
+				"
+				 ⛅️ wrangler x.x.x
+				──────────────────
+				Total Upload: xx KiB / gzip: xx KiB
+				Worker Startup Time: 100 ms
+				Your Worker has access to the following bindings:
+				Binding                       Resource
+				env.SECRET1 ("(hidden)")      Environment Variable
+				env.SECRET2 ("(hidden)")      Environment Variable
+
+				Uploaded test-name (TIMINGS)
+				Deployed test-name triggers (TIMINGS)
+				  https://test-name.test-sub-domain.workers.dev
+				Current Version ID: Galaxy-Class"
+			`);
 		});
 
 		it("should upload secrets from a .env file alongside the worker", async ({
@@ -193,22 +193,22 @@ SECRET3=value3`
 			await runWrangler(`deploy --secrets-file ${secretsFile}`);
 
 			expect(std.out).toMatchInlineSnapshot(`
-			"
-			 ⛅️ wrangler x.x.x
-			──────────────────
-			Total Upload: xx KiB / gzip: xx KiB
-			Worker Startup Time: 100 ms
-			Your Worker has access to the following bindings:
-			Binding                       Resource
-			env.SECRET1 ("(hidden)")      Environment Variable
-			env.SECRET2 ("(hidden)")      Environment Variable
-			env.SECRET3 ("(hidden)")      Environment Variable
-
-			Uploaded test-name (TIMINGS)
-			Deployed test-name triggers (TIMINGS)
-			  https://test-name.test-sub-domain.workers.dev
-			Current Version ID: Galaxy-Class"
-		`);
+				"
+				 ⛅️ wrangler x.x.x
+				──────────────────
+				Total Upload: xx KiB / gzip: xx KiB
+				Worker Startup Time: 100 ms
+				Your Worker has access to the following bindings:
+				Binding                       Resource
+				env.SECRET1 ("(hidden)")      Environment Variable
+				env.SECRET2 ("(hidden)")      Environment Variable
+				env.SECRET3 ("(hidden)")      Environment Variable
+
+				Uploaded test-name (TIMINGS)
+				Deployed test-name triggers (TIMINGS)
+				  https://test-name.test-sub-domain.workers.dev
+				Current Version ID: Galaxy-Class"
+			`);
 		});
 
 		it("should set keepSecrets to inherit non-provided secrets when providing secrets file", async ({
@@ -243,20 +243,20 @@ SECRET3=value3`
 			await runWrangler(`deploy --secrets-file ${secretsFile}`);
 
 			expect(std.out).toMatchInlineSnapshot(`
-			"
-			 ⛅️ wrangler x.x.x
-			──────────────────
-			Total Upload: xx KiB / gzip: xx KiB
-			Worker Startup Time: 100 ms
-			Your Worker has access to the following bindings:
-			Binding                         Resource
-			env.MY_SECRET ("(hidden)")      Environment Variable
-
-			Uploaded test-name (TIMINGS)
-			Deployed test-name triggers (TIMINGS)
-			  https://test-name.test-sub-domain.workers.dev
-			Current Version ID: Galaxy-Class"
-		`);
+				"
+				 ⛅️ wrangler x.x.x
+				──────────────────
+				Total Upload: xx KiB / gzip: xx KiB
+				Worker Startup Time: 100 ms
+				Your Worker has access to the following bindings:
+				Binding                         Resource
+				env.MY_SECRET ("(hidden)")      Environment Variable
+
+				Uploaded test-name (TIMINGS)
+				Deployed test-name triggers (TIMINGS)
+				  https://test-name.test-sub-domain.workers.dev
+				Current Version ID: Galaxy-Class"
+			`);
 		});
 
 		it("should fail when secrets file does not exist", async ({ expect }) => {
diff --git a/packages/wrangler/src/__tests__/deployments.test.ts b/packages/wrangler/src/__tests__/deployments.test.ts
index 7d4f03bfe1..782074afa8 100644
--- a/packages/wrangler/src/__tests__/deployments.test.ts
+++ b/packages/wrangler/src/__tests__/deployments.test.ts
@@ -70,7 +70,7 @@ describe("deployments", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]"
 		`);
 	});
diff --git a/packages/wrangler/src/__tests__/docs.test.ts b/packages/wrangler/src/__tests__/docs.test.ts
index 01afb83f48..b1e4d0a767 100644
--- a/packages/wrangler/src/__tests__/docs.test.ts
+++ b/packages/wrangler/src/__tests__/docs.test.ts
@@ -51,7 +51,7 @@ describe("wrangler docs", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]
 
 			OPTIONS
diff --git a/packages/wrangler/src/__tests__/experimental-commands-api.test.ts b/packages/wrangler/src/__tests__/experimental-commands-api.test.ts
index 53924cd5c5..4a2f2b845a 100644
--- a/packages/wrangler/src/__tests__/experimental-commands-api.test.ts
+++ b/packages/wrangler/src/__tests__/experimental-commands-api.test.ts
@@ -48,7 +48,7 @@ describe("experimental_getWranglerCommands", () => {
 			  },
 			  "install-skills": {
 			    "default": false,
-			    "describe": "Install Cloudflare agents skills, if not already present, without asking the user for confirmation",
+			    "describe": "Install Cloudflare skills for detected AI coding agents before running the command",
 			    "type": "boolean",
 			  },
 			  "v": {
diff --git a/packages/wrangler/src/__tests__/hyperdrive.test.ts b/packages/wrangler/src/__tests__/hyperdrive.test.ts
index 16ff3de5f9..9f5b1eb65b 100644
--- a/packages/wrangler/src/__tests__/hyperdrive.test.ts
+++ b/packages/wrangler/src/__tests__/hyperdrive.test.ts
@@ -46,7 +46,7 @@ describe("hyperdrive help", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]"
 		`);
 	});
@@ -82,7 +82,7 @@ describe("hyperdrive help", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]"
 		`);
 	});
diff --git a/packages/wrangler/src/__tests__/index.test.ts b/packages/wrangler/src/__tests__/index.test.ts
index 52b3d38c05..abd852bfa0 100644
--- a/packages/wrangler/src/__tests__/index.test.ts
+++ b/packages/wrangler/src/__tests__/index.test.ts
@@ -96,7 +96,7 @@ describe("wrangler", () => {
 				  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 				      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 				  -h, --help            Show help  [boolean]
-				      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+				      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 				  -v, --version         Show version number  [boolean]
 
 				Please report any issues to https://github.com/cloudflare/workers-sdk/issues/new/choose"
@@ -177,7 +177,7 @@ describe("wrangler", () => {
 				  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 				      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 				  -h, --help            Show help  [boolean]
-				      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+				      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 				  -v, --version         Show version number  [boolean]
 
 				Please report any issues to https://github.com/cloudflare/workers-sdk/issues/new/choose"
@@ -275,7 +275,7 @@ describe("wrangler", () => {
 				  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 				      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 				  -h, --help            Show help  [boolean]
-				      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+				      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 				  -v, --version         Show version number  [boolean]"
 			`);
 		});
@@ -302,7 +302,7 @@ describe("wrangler", () => {
 				  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 				      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 				  -h, --help            Show help  [boolean]
-				      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+				      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 				  -v, --version         Show version number  [boolean]"
 			`);
 		});
@@ -329,7 +329,7 @@ describe("wrangler", () => {
 				  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 				      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 				  -h, --help            Show help  [boolean]
-				      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+				      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 				  -v, --version         Show version number  [boolean]"
 			`);
 		});
@@ -355,7 +355,7 @@ describe("wrangler", () => {
 				  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 				      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 				  -h, --help            Show help  [boolean]
-				      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+				      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 				  -v, --version         Show version number  [boolean]"
 			`);
 		});
@@ -381,7 +381,7 @@ describe("wrangler", () => {
 				  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 				      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 				  -h, --help            Show help  [boolean]
-				      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+				      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 				  -v, --version         Show version number  [boolean]"
 			`);
 		});
diff --git a/packages/wrangler/src/__tests__/kv/help.test.ts b/packages/wrangler/src/__tests__/kv/help.test.ts
index 5dfce0af60..5a871f0cea 100644
--- a/packages/wrangler/src/__tests__/kv/help.test.ts
+++ b/packages/wrangler/src/__tests__/kv/help.test.ts
@@ -43,7 +43,7 @@ describe("kv", () => {
 				  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 				      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 				  -h, --help            Show help  [boolean]
-				      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+				      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 				  -v, --version         Show version number  [boolean]"
 			`);
 		});
@@ -67,7 +67,7 @@ describe("kv", () => {
 				  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 				      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 				  -h, --help            Show help  [boolean]
-				      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+				      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 				  -v, --version         Show version number  [boolean]"
 			`);
 		});
@@ -100,7 +100,7 @@ describe("kv", () => {
 				  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 				      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 				  -h, --help            Show help  [boolean]
-				      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+				      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 				  -v, --version         Show version number  [boolean]"
 			`);
 		});
diff --git a/packages/wrangler/src/__tests__/kv/key.test.ts b/packages/wrangler/src/__tests__/kv/key.test.ts
index c22ae4495e..34f7cdf2cf 100644
--- a/packages/wrangler/src/__tests__/kv/key.test.ts
+++ b/packages/wrangler/src/__tests__/kv/key.test.ts
@@ -413,7 +413,7 @@ describe("kv", () => {
 					  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 					      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 					  -h, --help            Show help  [boolean]
-					      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+					      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 					  -v, --version         Show version number  [boolean]
 
 					OPTIONS
@@ -463,7 +463,7 @@ describe("kv", () => {
 					  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 					      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 					  -h, --help            Show help  [boolean]
-					      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+					      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 					  -v, --version         Show version number  [boolean]
 
 					OPTIONS
@@ -515,7 +515,7 @@ describe("kv", () => {
 					  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 					      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 					  -h, --help            Show help  [boolean]
-					      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+					      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 					  -v, --version         Show version number  [boolean]
 
 					OPTIONS
@@ -565,7 +565,7 @@ describe("kv", () => {
 					  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 					      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 					  -h, --help            Show help  [boolean]
-					      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+					      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 					  -v, --version         Show version number  [boolean]
 
 					OPTIONS
@@ -612,7 +612,7 @@ describe("kv", () => {
 					  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 					      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 					  -h, --help            Show help  [boolean]
-					      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+					      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 					  -v, --version         Show version number  [boolean]
 
 					OPTIONS
@@ -664,7 +664,7 @@ describe("kv", () => {
 					  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 					      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 					  -h, --help            Show help  [boolean]
-					      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+					      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 					  -v, --version         Show version number  [boolean]
 
 					OPTIONS
@@ -1108,7 +1108,7 @@ describe("kv", () => {
 					  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 					      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 					  -h, --help            Show help  [boolean]
-					      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+					      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 					  -v, --version         Show version number  [boolean]
 
 					OPTIONS
@@ -1150,7 +1150,7 @@ describe("kv", () => {
 					  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 					      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 					  -h, --help            Show help  [boolean]
-					      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+					      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 					  -v, --version         Show version number  [boolean]
 
 					OPTIONS
@@ -1193,7 +1193,7 @@ describe("kv", () => {
 					  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 					      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 					  -h, --help            Show help  [boolean]
-					      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+					      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 					  -v, --version         Show version number  [boolean]
 
 					OPTIONS
diff --git a/packages/wrangler/src/__tests__/kv/namespace.test.ts b/packages/wrangler/src/__tests__/kv/namespace.test.ts
index 90cfd1ab48..425b611554 100644
--- a/packages/wrangler/src/__tests__/kv/namespace.test.ts
+++ b/packages/wrangler/src/__tests__/kv/namespace.test.ts
@@ -72,7 +72,7 @@ describe("kv", () => {
 					  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 					      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 					  -h, --help            Show help  [boolean]
-					      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+					      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 					  -v, --version         Show version number  [boolean]
 
 					OPTIONS
@@ -111,7 +111,7 @@ describe("kv", () => {
 					  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 					      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 					  -h, --help            Show help  [boolean]
-					      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+					      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 					  -v, --version         Show version number  [boolean]
 
 					OPTIONS
@@ -656,7 +656,7 @@ describe("kv", () => {
 					  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 					      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 					  -h, --help            Show help  [boolean]
-					      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+					      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 					  -v, --version         Show version number  [boolean]
 
 					OPTIONS
diff --git a/packages/wrangler/src/__tests__/mtls-certificates.test.ts b/packages/wrangler/src/__tests__/mtls-certificates.test.ts
index 0ac6d77692..0af380645f 100644
--- a/packages/wrangler/src/__tests__/mtls-certificates.test.ts
+++ b/packages/wrangler/src/__tests__/mtls-certificates.test.ts
@@ -420,7 +420,7 @@ describe("wrangler", () => {
 						  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 						      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 						  -h, --help            Show help  [boolean]
-						      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+						      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 						  -v, --version         Show version number  [boolean]"
 					`);
 				});
diff --git a/packages/wrangler/src/__tests__/pages/deploy.test.ts b/packages/wrangler/src/__tests__/pages/deploy.test.ts
index 9c11937f16..7a4711deb6 100644
--- a/packages/wrangler/src/__tests__/pages/deploy.test.ts
+++ b/packages/wrangler/src/__tests__/pages/deploy.test.ts
@@ -87,7 +87,7 @@ describe("pages deploy", () => {
 			      --cwd             Run as if Wrangler was started in the specified directory instead of the current working directory  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]
 
 			OPTIONS
diff --git a/packages/wrangler/src/__tests__/pages/pages.test.ts b/packages/wrangler/src/__tests__/pages/pages.test.ts
index 7cbbc7b55d..fdbb06f211 100644
--- a/packages/wrangler/src/__tests__/pages/pages.test.ts
+++ b/packages/wrangler/src/__tests__/pages/pages.test.ts
@@ -38,7 +38,7 @@ describe("pages", () => {
 			      --cwd             Run as if Wrangler was started in the specified directory instead of the current working directory  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]"
 		`);
 	});
@@ -62,7 +62,7 @@ describe("pages", () => {
 			      --cwd             Run as if Wrangler was started in the specified directory instead of the current working directory  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]
 
 			OPTIONS
@@ -112,7 +112,7 @@ describe("pages", () => {
 			      --cwd             Run as if Wrangler was started in the specified directory instead of the current working directory  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]"
 		`);
 	});
@@ -140,7 +140,7 @@ describe("pages", () => {
 			      --cwd             Run as if Wrangler was started in the specified directory instead of the current working directory  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]"
 		`);
 	});
@@ -163,7 +163,7 @@ describe("pages", () => {
 			      --cwd             Run as if Wrangler was started in the specified directory instead of the current working directory  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]
 
 			OPTIONS
@@ -199,7 +199,7 @@ describe("pages", () => {
 			      --cwd             Run as if Wrangler was started in the specified directory instead of the current working directory  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]"
 		`);
 	});
@@ -222,7 +222,7 @@ describe("pages", () => {
 			      --cwd             Run as if Wrangler was started in the specified directory instead of the current working directory  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]"
 		`);
 	});
diff --git a/packages/wrangler/src/__tests__/provision.test.ts b/packages/wrangler/src/__tests__/provision.test.ts
index c41692c502..b8fe6de57a 100644
--- a/packages/wrangler/src/__tests__/provision.test.ts
+++ b/packages/wrangler/src/__tests__/provision.test.ts
@@ -447,45 +447,45 @@ describe("resource provisioning", () => {
 			await runWrangler("deploy --x-auto-create=false");
 
 			expect(std.out).toMatchInlineSnapshot(`
-			"
-			 ⛅️ wrangler x.x.x
-			──────────────────
-			Total Upload: xx KiB / gzip: xx KiB
+				"
+				 ⛅️ wrangler x.x.x
+				──────────────────
+				Total Upload: xx KiB / gzip: xx KiB
 
-			Experimental: The following bindings need to be provisioned:
-			Binding        Resource
-			env.KV         KV Namespace
-			env.D1         D1 Database
-			env.R2         R2 Bucket
+				Experimental: The following bindings need to be provisioned:
+				Binding        Resource
+				env.KV         KV Namespace
+				env.D1         D1 Database
+				env.R2         R2 Bucket
 
 
-			Provisioning KV (KV Namespace)...
-			🌀 Creating new KV Namespace "new-kv"...
-			✨ KV provisioned 🎉
+				Provisioning KV (KV Namespace)...
+				🌀 Creating new KV Namespace "new-kv"...
+				✨ KV provisioned 🎉
 
-			Provisioning D1 (D1 Database)...
-			🌀 Creating new D1 Database "new-d1"...
-			✨ D1 provisioned 🎉
+				Provisioning D1 (D1 Database)...
+				🌀 Creating new D1 Database "new-d1"...
+				✨ D1 provisioned 🎉
 
-			Provisioning R2 (R2 Bucket)...
-			🌀 Creating new R2 Bucket "new-r2"...
-			✨ R2 provisioned 🎉
+				Provisioning R2 (R2 Bucket)...
+				🌀 Creating new R2 Bucket "new-r2"...
+				✨ R2 provisioned 🎉
 
-			Your Worker was deployed with provisioned resources. We've written the IDs of these resources to your config file, which you can choose to save or discard. Either way future deploys will continue to work.
-			🎉 All resources provisioned, continuing with deployment...
+				Your Worker was deployed with provisioned resources. We've written the IDs of these resources to your config file, which you can choose to save or discard. Either way future deploys will continue to work.
+				🎉 All resources provisioned, continuing with deployment...
 
-			Worker Startup Time: 100 ms
-			Your Worker has access to the following bindings:
-			Binding                 Resource
-			env.KV (new-kv-id)      KV Namespace
-			env.D1 (new-d1-id)      D1 Database
-			env.R2 (new-r2)         R2 Bucket
+				Worker Startup Time: 100 ms
+				Your Worker has access to the following bindings:
+				Binding                 Resource
+				env.KV (new-kv-id)      KV Namespace
+				env.D1 (new-d1-id)      D1 Database
+				env.R2 (new-r2)         R2 Bucket
 
-			Uploaded test-name (TIMINGS)
-			Deployed test-name triggers (TIMINGS)
-			  https://test-name.test-sub-domain.workers.dev
-			Current Version ID: Galaxy-Class"
-		`);
+				Uploaded test-name (TIMINGS)
+				Deployed test-name triggers (TIMINGS)
+				  https://test-name.test-sub-domain.workers.dev
+				Current Version ID: Galaxy-Class"
+			`);
 			expect(std.err).toMatchInlineSnapshot(`""`);
 			expect(std.warn).toMatchInlineSnapshot(`""`);
 
diff --git a/packages/wrangler/src/__tests__/queues/queues-subscription.test.ts b/packages/wrangler/src/__tests__/queues/queues-subscription.test.ts
index 6749a78f16..9d48168ecd 100644
--- a/packages/wrangler/src/__tests__/queues/queues-subscription.test.ts
+++ b/packages/wrangler/src/__tests__/queues/queues-subscription.test.ts
@@ -79,7 +79,7 @@ describe("queues subscription", () => {
 				  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 				      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 				  -h, --help            Show help  [boolean]
-				      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+				      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 				  -v, --version         Show version number  [boolean]
 
 				OPTIONS
@@ -258,7 +258,7 @@ describe("queues subscription", () => {
 				  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 				      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 				  -h, --help            Show help  [boolean]
-				      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+				      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 				  -v, --version         Show version number  [boolean]
 
 				OPTIONS
@@ -435,7 +435,7 @@ describe("queues subscription", () => {
 				  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 				      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 				  -h, --help            Show help  [boolean]
-				      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+				      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 				  -v, --version         Show version number  [boolean]
 
 				OPTIONS
@@ -556,7 +556,7 @@ describe("queues subscription", () => {
 				  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 				      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 				  -h, --help            Show help  [boolean]
-				      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+				      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 				  -v, --version         Show version number  [boolean]
 
 				OPTIONS
diff --git a/packages/wrangler/src/__tests__/queues/queues.test.ts b/packages/wrangler/src/__tests__/queues/queues.test.ts
index d019e4a209..36008b2325 100644
--- a/packages/wrangler/src/__tests__/queues/queues.test.ts
+++ b/packages/wrangler/src/__tests__/queues/queues.test.ts
@@ -51,7 +51,7 @@ describe("wrangler", () => {
 				  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 				      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 				  -h, --help            Show help  [boolean]
-				      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+				      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 				  -v, --version         Show version number  [boolean]"
 			`);
 		});
@@ -100,7 +100,7 @@ describe("wrangler", () => {
 					  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 					      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 					  -h, --help            Show help  [boolean]
-					      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+					      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 					  -v, --version         Show version number  [boolean]
 
 					OPTIONS
@@ -250,7 +250,7 @@ describe("wrangler", () => {
 					  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 					      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 					  -h, --help            Show help  [boolean]
-					      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+					      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 					  -v, --version         Show version number  [boolean]
 
 					OPTIONS
@@ -492,7 +492,7 @@ describe("wrangler", () => {
 					  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 					      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 					  -h, --help            Show help  [boolean]
-					      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+					      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 					  -v, --version         Show version number  [boolean]
 
 					OPTIONS
@@ -661,7 +661,7 @@ describe("wrangler", () => {
 					  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 					      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 					  -h, --help            Show help  [boolean]
-					      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+					      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 					  -v, --version         Show version number  [boolean]"
 				`);
 			});
@@ -736,7 +736,7 @@ describe("wrangler", () => {
 					  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 					      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 					  -h, --help            Show help  [boolean]
-					      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+					      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 					  -v, --version         Show version number  [boolean]"
 				`);
 			});
@@ -787,7 +787,7 @@ describe("wrangler", () => {
 						  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 						      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 						  -h, --help            Show help  [boolean]
-						      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+						      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 						  -v, --version         Show version number  [boolean]
 
 						OPTIONS
@@ -839,12 +839,12 @@ describe("wrangler", () => {
 					expect(postRequest.count).toEqual(1);
 
 					expect(std.out).toMatchInlineSnapshot(`
-					"
-					 ⛅️ wrangler x.x.x
-					──────────────────
-					Adding consumer to queue testQueue.
-					Added consumer to queue testQueue."
-				`);
+						"
+						 ⛅️ wrangler x.x.x
+						──────────────────
+						Adding consumer to queue testQueue.
+						Added consumer to queue testQueue."
+					`);
 				});
 
 				it("should add a consumer using custom values", async ({ expect }) => {
@@ -1152,7 +1152,7 @@ describe("wrangler", () => {
 						  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 						      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 						  -h, --help            Show help  [boolean]
-						      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+						      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 						  -v, --version         Show version number  [boolean]"
 					`);
 				});
@@ -1215,12 +1215,12 @@ describe("wrangler", () => {
 						expect(queueNameResolveRequest.count).toEqual(1);
 						expect(deleteRequest.count).toEqual(1);
 						expect(std.out).toMatchInlineSnapshot(`
-						"
-						 ⛅️ wrangler x.x.x
-						──────────────────
-						Removing consumer from queue testQueue.
-						Removed consumer from queue testQueue."
-					`);
+							"
+							 ⛅️ wrangler x.x.x
+							──────────────────
+							Removing consumer from queue testQueue.
+							Removed consumer from queue testQueue."
+						`);
 					});
 
 					it("should show error when deleting a non-existing consumer", async ({
@@ -1299,12 +1299,12 @@ describe("wrangler", () => {
 						expect(queueNameResolveRequest.count).toEqual(1);
 						expect(deleteRequest.count).toEqual(1);
 						expect(std.out).toMatchInlineSnapshot(`
-						"
-						 ⛅️ wrangler x.x.x
-						──────────────────
-						Removing consumer from queue testQueue.
-						Removed consumer from queue testQueue."
-					`);
+							"
+							 ⛅️ wrangler x.x.x
+							──────────────────
+							Removing consumer from queue testQueue.
+							Removed consumer from queue testQueue."
+						`);
 					});
 
 					it("should show error when deleting a non-matching environment", async ({
@@ -1584,7 +1584,7 @@ describe("wrangler", () => {
 					  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 					      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 					  -h, --help            Show help  [boolean]
-					      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+					      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 					  -v, --version         Show version number  [boolean]"
 				`);
 			});
@@ -1634,7 +1634,7 @@ describe("wrangler", () => {
 						  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 						      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 						  -h, --help            Show help  [boolean]
-						      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+						      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 						  -v, --version         Show version number  [boolean]
 
 						OPTIONS
@@ -1681,12 +1681,12 @@ describe("wrangler", () => {
 					expect(queueNameResolveRequest.count).toEqual(1);
 					expect(postRequest.count).toEqual(1);
 					expect(std.out).toMatchInlineSnapshot(`
-					"
-					 ⛅️ wrangler x.x.x
-					──────────────────
-					Adding consumer to queue testQueue.
-					Added consumer to queue testQueue."
-				`);
+						"
+						 ⛅️ wrangler x.x.x
+						──────────────────
+						Adding consumer to queue testQueue.
+						Added consumer to queue testQueue."
+					`);
 				});
 
 				it("should add a consumer using custom values", async ({ expect }) => {
@@ -1785,7 +1785,7 @@ describe("wrangler", () => {
 						  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 						      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 						  -h, --help            Show help  [boolean]
-						      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+						      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 						  -v, --version         Show version number  [boolean]"
 					`);
 				});
@@ -1875,7 +1875,7 @@ describe("wrangler", () => {
 					  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 					      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 					  -h, --help            Show help  [boolean]
-					      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+					      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 					  -v, --version         Show version number  [boolean]
 
 					OPTIONS
@@ -1971,7 +1971,7 @@ describe("wrangler", () => {
 					├─┼─┼─┼─┼─┼─┤
 					│ 1002 │ my-dlq │ 5 │ 2 │ 10000 │ 15 │
 					└─┴─┴─┴─┴─┴─┘"
-			`);
+				`);
 			});
 
 			it("should show empty message when queue has no consumers", async ({
@@ -2106,7 +2106,7 @@ describe("wrangler", () => {
 					  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 					      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 					  -h, --help            Show help  [boolean]
-					      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+					      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 					  -v, --version         Show version number  [boolean]
 
 					OPTIONS
@@ -2271,7 +2271,7 @@ describe("wrangler", () => {
 					  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 					      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 					  -h, --help            Show help  [boolean]
-					      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+					      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 					  -v, --version         Show version number  [boolean]
 
 					OPTIONS
@@ -2302,7 +2302,7 @@ describe("wrangler", () => {
 					├─┼─┼─┼─┼─┼─┤
 					│ 1002 │ my-dlq │ 5 │ 2 │ 10000 │ 15 │
 					└─┴─┴─┴─┴─┴─┘"
-			`);
+				`);
 			});
 
 			it("should show empty message when queue has no http consumers", async ({
@@ -2456,7 +2456,7 @@ describe("wrangler", () => {
 					  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 					      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 					  -h, --help            Show help  [boolean]
-					      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+					      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 					  -v, --version         Show version number  [boolean]"
 				`);
 			});
@@ -2636,7 +2636,7 @@ describe("wrangler", () => {
 				  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 				      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 				  -h, --help            Show help  [boolean]
-				      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+				      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 				  -v, --version         Show version number  [boolean]"
 			`);
 		});
@@ -2753,7 +2753,7 @@ describe("wrangler", () => {
 				  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 				      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 				  -h, --help            Show help  [boolean]
-				      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+				      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 				  -v, --version         Show version number  [boolean]"
 			`);
 		});
@@ -2862,7 +2862,7 @@ describe("wrangler", () => {
 				  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 				      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 				  -h, --help            Show help  [boolean]
-				      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+				      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 				  -v, --version         Show version number  [boolean]
 
 				OPTIONS
diff --git a/packages/wrangler/src/__tests__/r2/bucket.test.ts b/packages/wrangler/src/__tests__/r2/bucket.test.ts
index 5da8e87fe7..81d1c50680 100644
--- a/packages/wrangler/src/__tests__/r2/bucket.test.ts
+++ b/packages/wrangler/src/__tests__/r2/bucket.test.ts
@@ -127,7 +127,7 @@ describe("r2", () => {
 				  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 				      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 				  -h, --help            Show help  [boolean]
-				      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+				      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 				  -v, --version         Show version number  [boolean]"
 			`);
 		});
@@ -171,7 +171,7 @@ describe("r2", () => {
 				  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 				      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 				  -h, --help            Show help  [boolean]
-				      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+				      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 				  -v, --version         Show version number  [boolean]"
 			`);
 		});
@@ -351,7 +351,7 @@ describe("r2", () => {
 					  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 					      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 					  -h, --help            Show help  [boolean]
-					      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+					      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 					  -v, --version         Show version number  [boolean]
 
 					OPTIONS
@@ -390,7 +390,7 @@ describe("r2", () => {
 					  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 					      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 					  -h, --help            Show help  [boolean]
-					      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+					      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 					  -v, --version         Show version number  [boolean]
 
 					OPTIONS
@@ -526,7 +526,7 @@ describe("r2", () => {
 					  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 					      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 					  -h, --help            Show help  [boolean]
-					      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+					      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 					  -v, --version         Show version number  [boolean]"
 				`);
 				expect(std.err).toMatchInlineSnapshot(`
@@ -558,7 +558,7 @@ describe("r2", () => {
 						  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 						      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 						  -h, --help            Show help  [boolean]
-						      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+						      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 						  -v, --version         Show version number  [boolean]
 
 						OPTIONS
@@ -624,7 +624,7 @@ describe("r2", () => {
 					  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 					      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 					  -h, --help            Show help  [boolean]
-					      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+					      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 					  -v, --version         Show version number  [boolean]
 
 					OPTIONS
@@ -690,7 +690,7 @@ describe("r2", () => {
 					  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 					      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 					  -h, --help            Show help  [boolean]
-					      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+					      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 					  -v, --version         Show version number  [boolean]
 
 					OPTIONS
@@ -763,7 +763,7 @@ describe("r2", () => {
 					  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 					      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 					  -h, --help            Show help  [boolean]
-					      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+					      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 					  -v, --version         Show version number  [boolean]"
 				`);
 			});
@@ -867,7 +867,7 @@ describe("r2", () => {
 						  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 						      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 						  -h, --help            Show help  [boolean]
-						      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+						      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 						  -v, --version         Show version number  [boolean]
 
 						OPTIONS
@@ -1057,7 +1057,7 @@ describe("r2", () => {
 						  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 						      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 						  -h, --help            Show help  [boolean]
-						      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+						      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 						  -v, --version         Show version number  [boolean]
 
 						OPTIONS
@@ -1116,7 +1116,7 @@ describe("r2", () => {
 						  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 						      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 						  -h, --help            Show help  [boolean]
-						      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+						      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 						  -v, --version         Show version number  [boolean]
 
 						OPTIONS
@@ -1192,7 +1192,7 @@ describe("r2", () => {
 					  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 					      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 					  -h, --help            Show help  [boolean]
-					      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+					      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 					  -v, --version         Show version number  [boolean]"
 				`);
 			});
@@ -1255,7 +1255,7 @@ describe("r2", () => {
 						  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 						      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 						  -h, --help            Show help  [boolean]
-						      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+						      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 						  -v, --version         Show version number  [boolean]"
 					`);
 					expect(std.err).toMatchInlineSnapshot(`
@@ -1289,7 +1289,7 @@ describe("r2", () => {
 						  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 						      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 						  -h, --help            Show help  [boolean]
-						      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+						      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 						  -v, --version         Show version number  [boolean]"
 					`);
 					expect(std.err).toMatchInlineSnapshot(`
@@ -1388,7 +1388,7 @@ describe("r2", () => {
 						  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 						      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 						  -h, --help            Show help  [boolean]
-						      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+						      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 						  -v, --version         Show version number  [boolean]"
 					`);
 					expect(std.err).toMatchInlineSnapshot(`
@@ -1499,7 +1499,7 @@ describe("r2", () => {
 						  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 						      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 						  -h, --help            Show help  [boolean]
-						      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+						      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 						  -v, --version         Show version number  [boolean]"
 					`);
 				});
@@ -1578,7 +1578,7 @@ describe("r2", () => {
 							  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 							      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 							  -h, --help            Show help  [boolean]
-							      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+							      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 							  -v, --version         Show version number  [boolean]
 
 							OPTIONS
@@ -1715,7 +1715,7 @@ describe("r2", () => {
 							  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 							      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 							  -h, --help            Show help  [boolean]
-							      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+							      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 							  -v, --version         Show version number  [boolean]"
 						`);
 						expect(std.err).toMatchInlineSnapshot(`
@@ -1862,7 +1862,7 @@ describe("r2", () => {
 						  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 						      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 						  -h, --help            Show help  [boolean]
-						      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+						      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 						  -v, --version         Show version number  [boolean]"
 					`);
 				});
@@ -1993,7 +1993,7 @@ describe("r2", () => {
 							  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 							      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 							  -h, --help            Show help  [boolean]
-							      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+							      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 							  -v, --version         Show version number  [boolean]
 
 							OPTIONS
@@ -2113,7 +2113,7 @@ describe("r2", () => {
 							  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 							      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 							  -h, --help            Show help  [boolean]
-							      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+							      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 							  -v, --version         Show version number  [boolean]
 
 							OPTIONS
@@ -2417,7 +2417,7 @@ describe("r2", () => {
 						  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 						      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 						  -h, --help            Show help  [boolean]
-						      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+						      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 						  -v, --version         Show version number  [boolean]
 
 						OPTIONS
@@ -2792,7 +2792,7 @@ describe("r2", () => {
 						  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 						      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 						  -h, --help            Show help  [boolean]
-						      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+						      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 						  -v, --version         Show version number  [boolean]
 
 						OPTIONS
@@ -2959,7 +2959,7 @@ describe("r2", () => {
 						  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 						      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 						  -h, --help            Show help  [boolean]
-						      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+						      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 						  -v, --version         Show version number  [boolean]
 
 						OPTIONS
diff --git a/packages/wrangler/src/__tests__/r2/bulk.test.ts b/packages/wrangler/src/__tests__/r2/bulk.test.ts
index a44ba48449..40e3699d18 100644
--- a/packages/wrangler/src/__tests__/r2/bulk.test.ts
+++ b/packages/wrangler/src/__tests__/r2/bulk.test.ts
@@ -34,7 +34,7 @@ describe("r2", () => {
 				  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 				      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 				  -h, --help            Show help  [boolean]
-				      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+				      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 				  -v, --version         Show version number  [boolean]"
 			`);
 		});
diff --git a/packages/wrangler/src/__tests__/r2/help.test.ts b/packages/wrangler/src/__tests__/r2/help.test.ts
index ecde93149d..c1b5bec14c 100644
--- a/packages/wrangler/src/__tests__/r2/help.test.ts
+++ b/packages/wrangler/src/__tests__/r2/help.test.ts
@@ -31,7 +31,7 @@ describe("r2", () => {
 				  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 				      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 				  -h, --help            Show help  [boolean]
-				      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+				      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 				  -v, --version         Show version number  [boolean]"
 			`);
 		});
@@ -65,7 +65,7 @@ describe("r2", () => {
 				  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 				      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 				  -h, --help            Show help  [boolean]
-				      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+				      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 				  -v, --version         Show version number  [boolean]"
 			`);
 		});
diff --git a/packages/wrangler/src/__tests__/r2/local-uploads.test.ts b/packages/wrangler/src/__tests__/r2/local-uploads.test.ts
index 664f76c643..1dcf7137a5 100644
--- a/packages/wrangler/src/__tests__/r2/local-uploads.test.ts
+++ b/packages/wrangler/src/__tests__/r2/local-uploads.test.ts
@@ -38,7 +38,7 @@ describe("r2 bucket local-uploads", () => {
 				  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 				      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 				  -h, --help            Show help  [boolean]
-				      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+				      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 				  -v, --version         Show version number  [boolean]"
 			`);
 		});
diff --git a/packages/wrangler/src/__tests__/r2/object.test.ts b/packages/wrangler/src/__tests__/r2/object.test.ts
index d5436aa5c6..ebacfbcc76 100644
--- a/packages/wrangler/src/__tests__/r2/object.test.ts
+++ b/packages/wrangler/src/__tests__/r2/object.test.ts
@@ -41,7 +41,7 @@ describe("r2", () => {
 				  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 				      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 				  -h, --help            Show help  [boolean]
-				      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+				      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 				  -v, --version         Show version number  [boolean]"
 			`);
 		});
diff --git a/packages/wrangler/src/__tests__/register-yargs-command-skills.test.ts b/packages/wrangler/src/__tests__/register-yargs-command-skills.test.ts
index c44cb0b72e..6757faf8cc 100644
--- a/packages/wrangler/src/__tests__/register-yargs-command-skills.test.ts
+++ b/packages/wrangler/src/__tests__/register-yargs-command-skills.test.ts
@@ -1,6 +1,6 @@
 import { runInTempDir, seed } from "@cloudflare/workers-utils/test-helpers";
 import { beforeEach, describe, test, vi } from "vitest";
-import { maybeInstallCloudflareSkillsGlobally } from "../agents-skills-install";
+import { runSkillsInstallFlow } from "../agents-skills-install";
 import { mockConsoleMethods } from "./helpers/mock-console";
 import { runWrangler } from "./helpers/run-wrangler";
 
@@ -22,45 +22,104 @@ describe("register-yargs-command skills integration", () => {
 	mockConsoleMethods();
 
 	beforeEach(async () => {
-		// Seed a wrangler config so `wrangler setup` skips autoconfig and
-		// returns quickly — we only care about the skills install call.
 		await seed({
 			"wrangler.jsonc": JSON.stringify({ name: "test-worker" }),
 		});
 	});
 
-	test("calls maybeInstallCloudflareSkillsGlobally with false by default", async ({
+	test("does not call runSkillsInstallFlow for commands without suggestSkillsAfterHandler", async ({
 		expect,
 	}) => {
-		await runWrangler("setup");
+		// `wrangler complete` intentionally does not suggest skills because
+		// its stdout is captured by shell eval.
+		await runWrangler("complete zsh");
 
-		expect(maybeInstallCloudflareSkillsGlobally).toHaveBeenCalledWith(false);
+		expect(runSkillsInstallFlow).not.toHaveBeenCalled();
 	});
 
-	test("calls maybeInstallCloudflareSkillsGlobally with true when --install-skills is passed", async ({
+	test("calls runSkillsInstallFlow with force: true and command when --install-skills is passed", async ({
 		expect,
 	}) => {
-		await runWrangler("setup --install-skills");
+		// Use `complete` to isolate the --install-skills call from
+		// suggestSkillsAfterHandler (which complete does not have).
+		await runWrangler("complete zsh --install-skills");
 
-		expect(maybeInstallCloudflareSkillsGlobally).toHaveBeenCalledWith(true);
+		expect(runSkillsInstallFlow).toHaveBeenCalledWith({
+			force: true,
+			command: "complete",
+		});
 	});
 
-	test("does not call maybeInstallCloudflareSkillsGlobally for `wrangler complete`", async ({
+	test("calls runSkillsInstallFlow after commands with suggestSkillsAfterHandler: true", async ({
 		expect,
 	}) => {
-		// `wrangler complete zsh` output is captured by `eval "$(wrangler complete zsh)"`.
-		// The interactive skills prompt must not appear in that output.
-		await runWrangler("complete zsh");
+		await runWrangler("setup");
 
-		expect(maybeInstallCloudflareSkillsGlobally).not.toHaveBeenCalled();
+		expect(runSkillsInstallFlow).toHaveBeenCalledWith({
+			force: false,
+			command: "setup",
+			promptMessage: expect.any(Function),
+		});
+	});
+
+	test("calls runSkillsInstallFlow after `wrangler whoami` (non-JSON)", async ({
+		expect,
+	}) => {
+		// whoami in non-JSON mode completes successfully even without auth
+		// (it just prints "You are not authenticated") — the suggest-skills
+		// hook should still fire afterwards.
+		await runWrangler("whoami");
+
+		expect(runSkillsInstallFlow).toHaveBeenCalledWith({
+			force: false,
+			command: "whoami",
+			promptMessage: expect.any(Function),
+		});
 	});
 
-	test("still calls maybeInstallCloudflareSkillsGlobally when --install-skills is explicit on `wrangler complete`", async ({
+	test("command in skills install event contains only the command name, not positional args or flags", async ({
 		expect,
 	}) => {
-		// Explicit --install-skills should be honored even for `complete`.
+		// `wrangler complete zsh --install-skills` has:
+		//   - positional arg: "zsh"
+		//   - flag: "--install-skills"
+		// The `command` passed to runSkillsInstallFlow should be just the
+		// static command name from the definition ("complete"), with no
+		// positional arg values or flags leaked into it.
 		await runWrangler("complete zsh --install-skills");
 
-		expect(maybeInstallCloudflareSkillsGlobally).toHaveBeenCalledWith(true);
+		const call = vi.mocked(runSkillsInstallFlow).mock.calls[0][0];
+		expect(call.command).toBe("complete");
+		expect(call.command).not.toContain("zsh");
+		expect(call.command).not.toContain("install-skills");
+	});
+
+	test("does not call runSkillsInstallFlow after `wrangler whoami --json`", async ({
+		expect,
+	}) => {
+		// whoami --json without auth throws (non-zero exit), so we catch it.
+		// The suggestSkillsAfterHandler function returns false for --json,
+		// but the handler also throws, so the hook wouldn't run either way.
+		await expect(runWrangler("whoami --json")).rejects.toThrow();
+
+		expect(runSkillsInstallFlow).not.toHaveBeenCalled();
+	});
+
+	test("does not fail the command when runSkillsInstallFlow throws", async ({
+		expect,
+	}) => {
+		// If the post-handler skills suggestion fails (e.g. EACCES writing
+		// the metadata file, or an I/O error from the confirm prompt), the
+		// command itself should still succeed — the error is swallowed and
+		// logged at debug level.
+		vi.mocked(runSkillsInstallFlow).mockRejectedValueOnce(
+			new Error("EACCES: permission denied")
+		);
+
+		// `setup` has suggestSkillsAfterHandler: true, so it triggers the flow.
+		// This should resolve successfully despite the skills flow throwing.
+		await runWrangler("setup");
+
+		expect(runSkillsInstallFlow).toHaveBeenCalled();
 	});
 });
diff --git a/packages/wrangler/src/__tests__/secrets-store.test.ts b/packages/wrangler/src/__tests__/secrets-store.test.ts
index 4e40eef9b5..ffe7bc82ac 100644
--- a/packages/wrangler/src/__tests__/secrets-store.test.ts
+++ b/packages/wrangler/src/__tests__/secrets-store.test.ts
@@ -42,7 +42,7 @@ describe("secrets-store help", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]"
 		`);
 	});
@@ -73,7 +73,7 @@ describe("secrets-store help", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]"
 		`);
 	});
diff --git a/packages/wrangler/src/__tests__/setup.test.ts b/packages/wrangler/src/__tests__/setup.test.ts
index b6a5cb1da1..d0e0b0247b 100644
--- a/packages/wrangler/src/__tests__/setup.test.ts
+++ b/packages/wrangler/src/__tests__/setup.test.ts
@@ -42,7 +42,7 @@ describe("wrangler setup", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]
 
 			OPTIONS
diff --git a/packages/wrangler/src/__tests__/tunnel/tunnel.test.ts b/packages/wrangler/src/__tests__/tunnel/tunnel.test.ts
index 9ca7a24e3b..c5edac68dd 100644
--- a/packages/wrangler/src/__tests__/tunnel/tunnel.test.ts
+++ b/packages/wrangler/src/__tests__/tunnel/tunnel.test.ts
@@ -85,7 +85,7 @@ describe("tunnel help", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]"
 		`);
 	});
diff --git a/packages/wrangler/src/__tests__/vectorize/vectorize.test.ts b/packages/wrangler/src/__tests__/vectorize/vectorize.test.ts
index aba69d1445..2adfc22ad9 100644
--- a/packages/wrangler/src/__tests__/vectorize/vectorize.test.ts
+++ b/packages/wrangler/src/__tests__/vectorize/vectorize.test.ts
@@ -46,7 +46,7 @@ describe("vectorize help", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]"
 		`);
 	});
@@ -91,7 +91,7 @@ describe("vectorize help", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]"
 		`);
 	});
@@ -123,7 +123,7 @@ describe("vectorize help", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]
 
 			OPTIONS
@@ -159,7 +159,7 @@ describe("vectorize help", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]
 
 			OPTIONS
@@ -1090,7 +1090,7 @@ describe("vectorize commands", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]
 
 			OPTIONS
diff --git a/packages/wrangler/src/__tests__/versions/versions.help.test.ts b/packages/wrangler/src/__tests__/versions/versions.help.test.ts
index 6245d23311..fef5353f6f 100644
--- a/packages/wrangler/src/__tests__/versions/versions.help.test.ts
+++ b/packages/wrangler/src/__tests__/versions/versions.help.test.ts
@@ -29,7 +29,7 @@ describe("versions --help", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]"
 		`);
 	});
@@ -62,7 +62,7 @@ describe("versions subhelp", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]"
 		`);
 	});
diff --git a/packages/wrangler/src/__tests__/vitest.setup.ts b/packages/wrangler/src/__tests__/vitest.setup.ts
index 485225d939..d8f6ad7910 100644
--- a/packages/wrangler/src/__tests__/vitest.setup.ts
+++ b/packages/wrangler/src/__tests__/vitest.setup.ts
@@ -250,10 +250,7 @@ vi.mock("../metrics/metrics-config", async (importOriginal) => {
 vi.mock("../agents-skills-install", async (importOriginal) => {
 	const realModule =
 		await importOriginal<typeof import("../agents-skills-install")>();
-	vi.spyOn(
-		realModule,
-		"maybeInstallCloudflareSkillsGlobally"
-	).mockResolvedValue(undefined);
+	vi.spyOn(realModule, "runSkillsInstallFlow").mockResolvedValue(undefined);
 	vi.spyOn(realModule, "telemetryCurrentAgentSkillsInstalled").mockReturnValue(
 		Promise.resolve(null)
 	);
diff --git a/packages/wrangler/src/__tests__/vpc.test.ts b/packages/wrangler/src/__tests__/vpc.test.ts
index 3fa4b2c74a..53bb77780f 100644
--- a/packages/wrangler/src/__tests__/vpc.test.ts
+++ b/packages/wrangler/src/__tests__/vpc.test.ts
@@ -45,7 +45,7 @@ describe("vpc help", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]"
 		`);
 	});
@@ -75,7 +75,7 @@ describe("vpc help", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]"
 		`);
 	});
diff --git a/packages/wrangler/src/__tests__/worker-namespace.test.ts b/packages/wrangler/src/__tests__/worker-namespace.test.ts
index 3d56d00ccc..bbe80e18b1 100644
--- a/packages/wrangler/src/__tests__/worker-namespace.test.ts
+++ b/packages/wrangler/src/__tests__/worker-namespace.test.ts
@@ -54,7 +54,7 @@ describe("dispatch-namespace", () => {
 			  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 			      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 			  -h, --help            Show help  [boolean]
-			      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+			      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 			  -v, --version         Show version number  [boolean]",
 			  "warn": "",
 			}
@@ -109,7 +109,7 @@ describe("dispatch-namespace", () => {
 				  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 				      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 				  -h, --help            Show help  [boolean]
-				      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+				      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 				  -v, --version         Show version number  [boolean]"
 			`);
 		});
@@ -162,7 +162,7 @@ describe("dispatch-namespace", () => {
 				  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 				      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 				  -h, --help            Show help  [boolean]
-				      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+				      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 				  -v, --version         Show version number  [boolean]"
 			`);
 		});
@@ -224,7 +224,7 @@ describe("dispatch-namespace", () => {
 				  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 				      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 				  -h, --help            Show help  [boolean]
-				      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+				      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 				  -v, --version         Show version number  [boolean]"
 			`);
 		});
@@ -337,7 +337,7 @@ describe("dispatch-namespace", () => {
 				  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 				      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 				  -h, --help            Show help  [boolean]
-				      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+				      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 				  -v, --version         Show version number  [boolean]"
 			`);
 		});
diff --git a/packages/wrangler/src/__tests__/workflows.test.ts b/packages/wrangler/src/__tests__/workflows.test.ts
index e81af07edd..f50f2de03d 100644
--- a/packages/wrangler/src/__tests__/workflows.test.ts
+++ b/packages/wrangler/src/__tests__/workflows.test.ts
@@ -165,7 +165,7 @@ describe("wrangler workflows", () => {
 				  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 				      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 				  -h, --help            Show help  [boolean]
-				      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+				      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 				  -v, --version         Show version number  [boolean]"
 			`
 			);
@@ -201,7 +201,7 @@ describe("wrangler workflows", () => {
 				  -e, --env             Environment to use for operations, and for selecting .env and .dev.vars files  [string]
 				      --env-file        Path to an .env file to load - can be specified multiple times - values from earlier files are overridden by values in later files  [array]
 				  -h, --help            Show help  [boolean]
-				      --install-skills  Install Cloudflare agents skills, if not already present, without asking the user for confirmation  [boolean] [default: false]
+				      --install-skills  Install Cloudflare skills for detected AI coding agents before running the command  [boolean] [default: false]
 				  -v, --version         Show version number  [boolean]"
 			`);
 		});
diff --git a/packages/wrangler/src/agents-skills-install.ts b/packages/wrangler/src/agents-skills-install.ts
index 8ba80be4d7..828998c8ca 100644
--- a/packages/wrangler/src/agents-skills-install.ts
+++ b/packages/wrangler/src/agents-skills-install.ts
@@ -15,20 +15,53 @@ import { logger } from "./logger";
 import { sendMetricsEvent } from "./metrics";
 
 /**
- * Detects AI coding agents installed on the user's machine and, if
- * appropriate, offers to install Cloudflare skill files into their global
- * skills directories.
+ * Options for {@link runSkillsInstallFlow}.
  *
- * Skills are installed via the rosie-skills JS API, which handles
- * downloading from the `cloudflare/skills` GitHub repository, agent
- * detection, and file placement.
+ * When `force` is `true`, the interactive prompt is skipped entirely so no
+ * `promptMessage` is needed. When `force` is `false`, a `promptMessage`
+ * function must be provided to generate the confirmation prompt shown to the user.
+ */
+type SkillsInstallFlowOptions =
+	| {
+			/** Skip the interactive prompt and install unconditionally. Metadata and CI checks are also bypassed. */
+			force: true;
+			/**
+			 * The wrangler command that triggered the skills install flow
+			 * (e.g. `"deploy"`, `"dev"`). Included in telemetry events so
+			 * we can correlate skills installs with the commands that prompted them.
+			 */
+			command?: string;
+	  }
+	| {
+			/** Show the interactive prompt before installing. */
+			force: false;
+			/**
+			 * The wrangler command that triggered the skills install flow
+			 * (e.g. `"deploy"`, `"dev"`). Included in telemetry events so
+			 * we can correlate skills installs with the commands that prompted them.
+			 */
+			command?: string;
+			/**
+			 * Returns the confirmation prompt message shown to the user.
+			 *
+			 * @param agentNames - Display names of the detected agents.
+			 * @returns The prompt string passed to {@link confirm}.
+			 */
+			promptMessage: (agentNames: string[]) => string;
+	  };
+
+/**
+ * Shared implementation for skills installation flows. Handles guard checks
+ * (metadata, CI, agent detection, interactivity), prompts the user with a
+ * caller-provided message, and performs the installation via rosie.
  *
- * @param force - When `true` the interactive prompt is skipped and skills are
- *   installed unconditionally (used by `--install-skills`).
+ * @param options - Controls whether to force-install and what prompt to show.
  */
-export async function maybeInstallCloudflareSkillsGlobally(
-	force: boolean
+export async function runSkillsInstallFlow(
+	options: SkillsInstallFlowOptions
 ): Promise<void> {
+	const { force, command } = options;
+
 	const sendResultMetricsEvent = (
 		result:
 			| { skippedBecause: string; errorMessage?: string }
@@ -42,6 +75,7 @@ export async function maybeInstallCloudflareSkillsGlobally(
 				{
 					reason: result.skippedBecause,
 					...(result.errorMessage ? { errorMessage: result.errorMessage } : {}),
+					...(command ? { command } : {}),
 				},
 				{}
 			);
@@ -50,6 +84,7 @@ export async function maybeInstallCloudflareSkillsGlobally(
 				"skills_install_completed",
 				{
 					agents: result.targetedAgents,
+					...(command ? { command } : {}),
 				},
 				{}
 			);
@@ -95,12 +130,28 @@ export async function maybeInstallCloudflareSkillsGlobally(
 		return;
 	}
 
-	const accepted =
-		force ||
-		(await confirm(
-			`Wrangler detected the following AI coding agents: ${detectedAgents.map(({ name }) => name).join(", ")}. Would you like to install Cloudflare skills for them?`,
-			{ defaultValue: true, fallbackValue: false }
-		));
+	let accepted: boolean;
+	if (force) {
+		accepted = true;
+	} else {
+		// Persist an "unanswered" marker *before* showing the prompt so that if
+		// the user interrupts the process (CTRL+C, terminal closed, etc.) the
+		// metadata file already exists and the prompt won't reappear next time.
+		writeSkillsInstallMetadataFile({
+			version: 1,
+			accepted: "unanswered",
+			date: new Date().toISOString(),
+			detectedAgents,
+		});
+
+		logger.log();
+
+		const agentDisplayNames = detectedAgents.map(({ name }) => name);
+		accepted = await confirm(options.promptMessage(agentDisplayNames), {
+			defaultValue: true,
+			fallbackValue: false,
+		});
+	}
 
 	if (!accepted) {
 		writeSkillsInstallMetadataFile({
@@ -119,6 +170,10 @@ export async function maybeInstallCloudflareSkillsGlobally(
 			global: true,
 			agent: agentNames,
 			lockfile: false,
+			// rosie shows a bunch of extra logs regarding the installation
+			// we do not want to show them as standard output so we just log
+			// them at the debug level
+			onLog: ({ message }) => logger.debug(message),
 		});
 
 		const failedSet = new Set(failedAgents);
@@ -128,11 +183,12 @@ export async function maybeInstallCloudflareSkillsGlobally(
 
 		if (succeededAgents.length > 0) {
 			logger.log(
-				`Successfully installed Cloudflare skills for: ${succeededAgents.map(({ name }) => name).join(", ")}.`
+				`\n🚀 Successfully installed Cloudflare skills for: ${succeededAgents.map(({ name }) => name).join(", ")}.\n`
 			);
 		}
 
 		if (failedAgents.length > 0) {
+			logger.log();
 			logger.warn(
 				`Skills installation failed for agents: ${failedAgents.join(", ")}.`
 			);
@@ -171,6 +227,24 @@ export async function maybeInstallCloudflareSkillsGlobally(
 	}
 }
 
+/**
+ * Builds the confirmation prompt shown to the user after a wrangler command
+ * completes, asking whether to install Cloudflare skills for detected AI
+ * coding agents.
+ *
+ * Used as the {@link SkillsInstallFlowOptions.promptMessage} callback when
+ * skills installation is suggested via `suggestSkillsAfterHandler`.
+ *
+ * @param agentNames - Display names of the detected AI coding agents
+ *   (e.g. `["Claude Code", "Cursor"]`).
+ * @returns The formatted confirmation prompt string passed to {@link confirm}.
+ */
+export function skillInstallPromptMessageAfterWranglerCommandHandler(
+	agentNames: string[]
+): string {
+	return `Before you go, Wrangler detected AI coding agents that may not be best configured to work with Cloudflare: ${agentNames.join(", ")}. Would you like Wrangler to automatically install Cloudflare skills for the best experience?`;
+}
+
 /** The GitHub repo spec for Cloudflare skills, used with rosie.install(). */
 const SKILLS_REPO = "cloudflare/skills";
 
@@ -200,8 +274,17 @@ type AgentInfo = {
 interface SkillsInstallMetadata {
 	/** Schema version for forward-compatibility. Currently always `1`. */
 	version: 1;
-	/** Whether the user accepted the prompt to install skills. */
-	accepted: boolean;
+	/**
+	 * Whether the user accepted the prompt to install skills.
+	 *
+	 * - `true`  — the user accepted and installation was attempted.
+	 * - `false` — the user explicitly declined.
+	 * - `"unanswered"` — the metadata file was written before the prompt was
+	 *   shown but the user never answered (e.g. CTRL+C, terminal closed).
+	 *   Treated the same as a decline for the purpose of suppressing future
+	 *   prompts.
+	 */
+	accepted: boolean | "unanswered";
 	/** ISO date string of when the user was prompted. */
 	date: string;
 	/** All agents detected on the user's machine. */
@@ -653,7 +736,7 @@ async function computeTelemetryCurrentAgentSkillsInstalled(): Promise<AgentSkill
 		// happens to match this alternative path (e.g. OpenCode reads
 		// ~/.agents/skills, which is Warp's rosie install target).
 		const metadata = readSkillsInstallMetadataFile();
-		if (metadata?.accepted) {
+		if (metadata?.accepted === true) {
 			const altAbsPath = path.resolve(matchedAlternativePath);
 			const wasInstalledForAnotherAgent = metadata.detectedAgents?.some(
 				(agent) => {
@@ -700,7 +783,7 @@ async function computeTelemetryCurrentAgentSkillsInstalled(): Promise<AgentSkill
 			));
 
 	if (
-		metadata.accepted &&
+		metadata.accepted === true &&
 		isInDetectedAgents === true &&
 		!installFailedForAgent
 	) {
diff --git a/packages/wrangler/src/build/index.ts b/packages/wrangler/src/build/index.ts
index 0409aa4017..fffb1f4019 100644
--- a/packages/wrangler/src/build/index.ts
+++ b/packages/wrangler/src/build/index.ts
@@ -12,6 +12,7 @@ export const buildCommand = createCommand({
 	behaviour: {
 		printBanner: false,
 		provideConfig: false,
+		suggestSkillsAfterHandler: true,
 	},
 	args: {
 		...experimentalNewConfigArg,
diff --git a/packages/wrangler/src/check/commands.ts b/packages/wrangler/src/check/commands.ts
index ab90353c89..62a7ac6044 100644
--- a/packages/wrangler/src/check/commands.ts
+++ b/packages/wrangler/src/check/commands.ts
@@ -141,6 +141,9 @@ export const checkStartupCommand = createCommand({
 		owner: "Workers: Authoring and Testing",
 		status: "alpha",
 	},
+	behaviour: {
+		suggestSkillsAfterHandler: true,
+	},
 	handler: checkStartupHandler,
 });
 
diff --git a/packages/wrangler/src/complete.ts b/packages/wrangler/src/complete.ts
index 0d9c48e269..97cecf971e 100644
--- a/packages/wrangler/src/complete.ts
+++ b/packages/wrangler/src/complete.ts
@@ -132,7 +132,6 @@ export const completionsCommand = createCommand({
 	behaviour: {
 		printBanner: false,
 		provideConfig: false,
-		skipSkillsPrompt: true,
 	},
 	positionalArgs: ["shell"],
 	args: {
diff --git a/packages/wrangler/src/core/register-yargs-command.ts b/packages/wrangler/src/core/register-yargs-command.ts
index 1580d3c44d..62e08e7bef 100644
--- a/packages/wrangler/src/core/register-yargs-command.ts
+++ b/packages/wrangler/src/core/register-yargs-command.ts
@@ -8,7 +8,10 @@ import {
 	UserError,
 } from "@cloudflare/workers-utils";
 import chalk from "chalk";
-import { maybeInstallCloudflareSkillsGlobally } from "../agents-skills-install";
+import {
+	runSkillsInstallFlow,
+	skillInstallPromptMessageAfterWranglerCommandHandler,
+} from "../agents-skills-install";
 import {
 	fetchKVGetValue,
 	fetchResult,
@@ -149,8 +152,8 @@ function createHandler(def: InternalCommandDefinition, argv: string[]) {
 				await printWranglerBanner();
 			}
 
-			if (!def.behaviour?.skipSkillsPrompt || args.installSkills) {
-				await maybeInstallCloudflareSkillsGlobally(args.installSkills);
+			if (args.installSkills) {
+				await runSkillsInstallFlow({ force: true, command: sanitizedCommand });
 			}
 
 			if (!getWranglerHideBanner()) {
@@ -320,6 +323,28 @@ function createHandler(def: InternalCommandDefinition, argv: string[]) {
 						def.behaviour
 					);
 
+					const shouldSuggestSkills =
+						def.behaviour?.suggestSkillsAfterHandler ?? false;
+					const suggestSkillsEnabled =
+						shouldSuggestSkills === true ||
+						(typeof shouldSuggestSkills === "function" &&
+							shouldSuggestSkills(args) === true);
+
+					if (suggestSkillsEnabled) {
+						try {
+							await runSkillsInstallFlow({
+								force: false,
+								command: sanitizedCommand,
+								promptMessage:
+									skillInstallPromptMessageAfterWranglerCommandHandler,
+							});
+						} catch (skillsErr) {
+							logger.debug(
+								`Skills suggestion failed: ${skillsErr instanceof Error ? skillsErr.message : skillsErr}`
+							);
+						}
+					}
+
 					return result;
 				} catch (err) {
 					// If the error is already a CommandHandledError (e.g., from a nested wrangler.parse() call),
diff --git a/packages/wrangler/src/core/types.ts b/packages/wrangler/src/core/types.ts
index c0bbe7107a..7893c2e23c 100644
--- a/packages/wrangler/src/core/types.ts
+++ b/packages/wrangler/src/core/types.ts
@@ -225,12 +225,19 @@ export type CommandDefinition<
 		sendMetrics?: boolean;
 
 		/**
-		 * Skip the AI coding agent skills installation prompt for this command.
-		 * Set to `true` for commands whose stdout is captured by the shell (e.g. `complete`),
-		 * where interactive prompts would corrupt the output.
+		 * After the command handler completes successfully, suggest installing
+		 * Cloudflare skills for detected AI coding agents that don't have them.
+		 *
+		 * When set to `true`, the suggestion always runs after the handler.
+		 * When set to a function, it receives the parsed args and should return
+		 * `true` to enable the suggestion — use this to skip the prompt in modes
+		 * where interactive output is inappropriate (e.g. `--json`).
+		 *
 		 * @default false
 		 */
-		skipSkillsPrompt?: boolean;
+		suggestSkillsAfterHandler?:
+			| boolean
+			| ((args: HandlerArgs<NamedArgDefs>) => boolean);
 	};
 
 	/**
diff --git a/packages/wrangler/src/delete.ts b/packages/wrangler/src/delete.ts
index 495fcc10e0..38f66ef86f 100644
--- a/packages/wrangler/src/delete.ts
+++ b/packages/wrangler/src/delete.ts
@@ -65,6 +65,9 @@ export const deleteCommand = createCommand({
 		status: "stable",
 		category: "Compute & AI",
 	},
+	behaviour: {
+		suggestSkillsAfterHandler: true,
+	},
 	args: {
 		script: {
 			describe: "The path to an entry point for your worker",
diff --git a/packages/wrangler/src/deploy/index.ts b/packages/wrangler/src/deploy/index.ts
index ea070958ed..4c80437830 100644
--- a/packages/wrangler/src/deploy/index.ts
+++ b/packages/wrangler/src/deploy/index.ts
@@ -107,6 +107,7 @@ export const deployCommand = createCommand({
 		}),
 		warnIfMultipleEnvsConfiguredButNoneSpecified: true,
 		printMetricsBanner: true,
+		suggestSkillsAfterHandler: true,
 	},
 	validateArgs(args) {
 		validateDeployVersionsArgs(args, "deploy");
diff --git a/packages/wrangler/src/docs/index.ts b/packages/wrangler/src/docs/index.ts
index d5c116519f..03b4898caf 100644
--- a/packages/wrangler/src/docs/index.ts
+++ b/packages/wrangler/src/docs/index.ts
@@ -25,6 +25,7 @@ export const docs = createCommand({
 	},
 	behaviour: {
 		printMetricsBanner: true,
+		suggestSkillsAfterHandler: true,
 	},
 	positionalArgs: ["search"],
 	async handler(args, { config }) {
diff --git a/packages/wrangler/src/index.ts b/packages/wrangler/src/index.ts
index 59913c3b81..6eadcb12d3 100644
--- a/packages/wrangler/src/index.ts
+++ b/packages/wrangler/src/index.ts
@@ -549,7 +549,7 @@ export function createCLIParser(argv: string[]) {
 		},
 		"install-skills": {
 			describe:
-				"Install Cloudflare agents skills, if not already present, without asking the user for confirmation",
+				"Install Cloudflare skills for detected AI coding agents before running the command",
 			type: "boolean",
 			default: false,
 		},
diff --git a/packages/wrangler/src/init.ts b/packages/wrangler/src/init.ts
index 4bea0ef8cf..01ccace627 100644
--- a/packages/wrangler/src/init.ts
+++ b/packages/wrangler/src/init.ts
@@ -56,6 +56,7 @@ export const init = createCommand({
 	},
 	behaviour: {
 		provideConfig: false,
+		suggestSkillsAfterHandler: true,
 	},
 	positionalArgs: ["name"],
 	async handler(args) {
diff --git a/packages/wrangler/src/metrics/commands.ts b/packages/wrangler/src/metrics/commands.ts
index aeca13b23e..c32320bfab 100644
--- a/packages/wrangler/src/metrics/commands.ts
+++ b/packages/wrangler/src/metrics/commands.ts
@@ -29,6 +29,7 @@ export const telemetryDisableCommand = createCommand({
 	},
 	behaviour: {
 		sendMetrics: false,
+		suggestSkillsAfterHandler: true,
 	},
 	async handler() {
 		updateMetricsPermission(false);
@@ -45,6 +46,9 @@ export const telemetryEnableCommand = createCommand({
 		owner: "Workers: Authoring and Testing",
 		status: "stable",
 	},
+	behaviour: {
+		suggestSkillsAfterHandler: true,
+	},
 	async handler() {
 		updateMetricsPermission(true);
 		logTelemetryStatus(true);
@@ -60,6 +64,9 @@ export const telemetryStatusCommand = createCommand({
 		owner: "Workers: Authoring and Testing",
 		status: "stable",
 	},
+	behaviour: {
+		suggestSkillsAfterHandler: true,
+	},
 	async handler(_, { config }) {
 		const savedConfig = readMetricsConfig();
 		const sendMetricsEnv = getWranglerSendMetricsFromEnv();
diff --git a/packages/wrangler/src/preview/index.ts b/packages/wrangler/src/preview/index.ts
index e2ddd94f32..b32ffd673a 100644
--- a/packages/wrangler/src/preview/index.ts
+++ b/packages/wrangler/src/preview/index.ts
@@ -61,6 +61,7 @@ export const previewCommand = createCommand({
 	behaviour: {
 		useConfigRedirectIfAvailable: true,
 		printBanner: (args) => args.json !== true,
+		suggestSkillsAfterHandler: (args) => args.json !== true,
 	},
 	handler: handlePreviewCommand,
 });
@@ -92,6 +93,9 @@ export const previewDeleteCommand = createCommand({
 			requiresArg: true,
 		},
 	},
+	behaviour: {
+		suggestSkillsAfterHandler: true,
+	},
 	handler: handlePreviewDeleteCommand,
 });
 
@@ -117,6 +121,9 @@ export const previewSettingsUpdateCommand = createCommand({
 			alias: "y",
 		},
 	},
+	behaviour: {
+		suggestSkillsAfterHandler: true,
+	},
 	handler: handlePreviewSettingsUpdateCommand,
 });
 
@@ -142,6 +149,7 @@ export const previewSettingsCommand = createCommand({
 	},
 	behaviour: {
 		printBanner: (args) => args.json !== true,
+		suggestSkillsAfterHandler: (args) => args.json !== true,
 	},
 	handler: handlePreviewSettingsCommand,
 });
@@ -176,6 +184,9 @@ export const previewSecretPutCommand = createCommand({
 			requiresArg: true,
 		},
 	},
+	behaviour: {
+		suggestSkillsAfterHandler: true,
+	},
 	handler: handlePreviewSecretPutCommand,
 });
 
@@ -206,6 +217,9 @@ export const previewSecretDeleteCommand = createCommand({
 			requiresArg: true,
 		},
 	},
+	behaviour: {
+		suggestSkillsAfterHandler: true,
+	},
 	handler: handlePreviewSecretDeleteCommand,
 });
 
@@ -231,6 +245,7 @@ export const previewSecretListCommand = createCommand({
 	},
 	behaviour: {
 		printBanner: (args) => args.json !== true,
+		suggestSkillsAfterHandler: (args) => args.json !== true,
 	},
 	handler: handlePreviewSecretListCommand,
 });
@@ -255,5 +270,8 @@ export const previewSecretBulkCommand = createCommand({
 			requiresArg: true,
 		},
 	},
+	behaviour: {
+		suggestSkillsAfterHandler: true,
+	},
 	handler: handlePreviewSecretBulkCommand,
 });
diff --git a/packages/wrangler/src/secret/index.ts b/packages/wrangler/src/secret/index.ts
index 6da9bbef92..46186b327d 100644
--- a/packages/wrangler/src/secret/index.ts
+++ b/packages/wrangler/src/secret/index.ts
@@ -100,6 +100,7 @@ export const secretPutCommand = createCommand({
 	positionalArgs: ["key"],
 	behaviour: {
 		warnIfMultipleEnvsConfiguredButNoneSpecified: true,
+		suggestSkillsAfterHandler: true,
 	},
 	args: {
 		key: {
@@ -230,6 +231,7 @@ export const secretDeleteCommand = createCommand({
 	positionalArgs: ["key"],
 	behaviour: {
 		warnIfMultipleEnvsConfiguredButNoneSpecified: true,
+		suggestSkillsAfterHandler: true,
 	},
 	args: {
 		key: {
@@ -329,6 +331,7 @@ export const secretListCommand = createCommand({
 	},
 	behaviour: {
 		printBanner: (args) => args.format === "pretty",
+		suggestSkillsAfterHandler: (args) => args.format === "pretty",
 	},
 	async handler(args, { config }) {
 		if (config.pages_build_output_dir) {
@@ -431,6 +434,7 @@ export const secretBulkCommand = createCommand({
 	positionalArgs: ["file"],
 	behaviour: {
 		warnIfMultipleEnvsConfiguredButNoneSpecified: true,
+		suggestSkillsAfterHandler: true,
 	},
 	args: {
 		file: {
diff --git a/packages/wrangler/src/setup.ts b/packages/wrangler/src/setup.ts
index 30e804c4b0..fe842f2b3f 100644
--- a/packages/wrangler/src/setup.ts
+++ b/packages/wrangler/src/setup.ts
@@ -17,6 +17,9 @@ export const setupCommand = createCommand({
 		status: "stable",
 		category: "Compute & AI",
 	},
+	behaviour: {
+		suggestSkillsAfterHandler: true,
+	},
 	args: {
 		yes: {
 			describe: 'Answer "yes" to any prompts for configuring your project',
diff --git a/packages/wrangler/src/triggers/index.ts b/packages/wrangler/src/triggers/index.ts
index c2486e2b40..d7fe8ddf7e 100644
--- a/packages/wrangler/src/triggers/index.ts
+++ b/packages/wrangler/src/triggers/index.ts
@@ -60,6 +60,7 @@ export const triggersDeployCommand = createCommand({
 	},
 	behaviour: {
 		warnIfMultipleEnvsConfiguredButNoneSpecified: true,
+		suggestSkillsAfterHandler: true,
 	},
 	async handler(args, { config }) {
 		metrics.sendMetricsEvent("deploy worker triggers", {
diff --git a/packages/wrangler/src/type-generation/index.ts b/packages/wrangler/src/type-generation/index.ts
index eea03d3859..444dd9e897 100644
--- a/packages/wrangler/src/type-generation/index.ts
+++ b/packages/wrangler/src/type-generation/index.ts
@@ -114,6 +114,7 @@ export const typesCommand = createCommand({
 	},
 	behaviour: {
 		provideConfig: false,
+		suggestSkillsAfterHandler: true,
 	},
 	positionalArgs: ["path"],
 	args: {
diff --git a/packages/wrangler/src/user/commands.ts b/packages/wrangler/src/user/commands.ts
index 4a04cfc8cd..670e11bcf6 100644
--- a/packages/wrangler/src/user/commands.ts
+++ b/packages/wrangler/src/user/commands.ts
@@ -30,6 +30,7 @@ export const loginCommand = createCommand({
 	},
 	behaviour: {
 		printConfigWarnings: false,
+		suggestSkillsAfterHandler: true,
 	},
 	args: {
 		"scopes-list": {
@@ -110,6 +111,7 @@ export const logoutCommand = createCommand({
 	behaviour: {
 		printConfigWarnings: false,
 		provideConfig: false,
+		suggestSkillsAfterHandler: true,
 	},
 	async handler() {
 		await logout();
@@ -137,6 +139,7 @@ export const whoamiCommand = createCommand({
 	behaviour: {
 		printBanner: (args) => !args.json,
 		printConfigWarnings: false,
+		suggestSkillsAfterHandler: (args) => !args.json,
 	},
 	args: {
 		account: {
@@ -177,6 +180,7 @@ export const authTokenCommand = createCommand({
 	behaviour: {
 		printBanner: (args) => !args.json,
 		printConfigWarnings: false,
+		suggestSkillsAfterHandler: (args) => !args.json,
 	},
 	args: {
 		json: {
diff --git a/packages/wrangler/src/versions/deploy.ts b/packages/wrangler/src/versions/deploy.ts
index 5a528046dc..549308ecd6 100644
--- a/packages/wrangler/src/versions/deploy.ts
+++ b/packages/wrangler/src/versions/deploy.ts
@@ -43,6 +43,7 @@ export const versionsDeployCommand = createCommand({
 	behaviour: {
 		useConfigRedirectIfAvailable: true,
 		warnIfMultipleEnvsConfiguredButNoneSpecified: true,
+		suggestSkillsAfterHandler: true,
 	},
 
 	args: {
diff --git a/packages/wrangler/src/versions/deployments/list.ts b/packages/wrangler/src/versions/deployments/list.ts
index fd546b024d..805afbd5a3 100644
--- a/packages/wrangler/src/versions/deployments/list.ts
+++ b/packages/wrangler/src/versions/deployments/list.ts
@@ -32,6 +32,7 @@ export const deploymentsListCommand = createCommand({
 	},
 	behaviour: {
 		printBanner: (args) => !args.json,
+		suggestSkillsAfterHandler: (args) => !args.json,
 	},
 	handler: async function versionsDeploymentsListHandler(args, { config }) {
 		metrics.sendMetricsEvent(
diff --git a/packages/wrangler/src/versions/deployments/status.ts b/packages/wrangler/src/versions/deployments/status.ts
index 55191cc7a4..095e80d902 100644
--- a/packages/wrangler/src/versions/deployments/status.ts
+++ b/packages/wrangler/src/versions/deployments/status.ts
@@ -32,6 +32,7 @@ export const deploymentsStatusCommand = createCommand({
 	},
 	behaviour: {
 		printBanner: (args) => !args.json,
+		suggestSkillsAfterHandler: (args) => !args.json,
 	},
 	handler: async function versionsDeploymentsStatusHandler(args, { config }) {
 		metrics.sendMetricsEvent("view latest versioned deployment", {
diff --git a/packages/wrangler/src/versions/deployments/view.ts b/packages/wrangler/src/versions/deployments/view.ts
index 104aaa0b46..f8fecabbfb 100644
--- a/packages/wrangler/src/versions/deployments/view.ts
+++ b/packages/wrangler/src/versions/deployments/view.ts
@@ -8,6 +8,9 @@ export const deploymentsViewCommand = createCommand({
 		status: "stable",
 		hidden: true,
 	},
+	behaviour: {
+		suggestSkillsAfterHandler: true,
+	},
 	args: {
 		name: {
 			describe: "Name of the Worker",
diff --git a/packages/wrangler/src/versions/list.ts b/packages/wrangler/src/versions/list.ts
index 1e71918351..43baf59166 100644
--- a/packages/wrangler/src/versions/list.ts
+++ b/packages/wrangler/src/versions/list.ts
@@ -18,6 +18,7 @@ export const versionsListCommand = createCommand({
 	},
 	behaviour: {
 		printBanner: (args) => !args.json,
+		suggestSkillsAfterHandler: (args) => !args.json,
 	},
 	args: {
 		name: {
diff --git a/packages/wrangler/src/versions/rollback/index.ts b/packages/wrangler/src/versions/rollback/index.ts
index 1e81aad16a..222abb57d7 100644
--- a/packages/wrangler/src/versions/rollback/index.ts
+++ b/packages/wrangler/src/versions/rollback/index.ts
@@ -43,6 +43,9 @@ export const versionsRollbackCommand = createCommand({
 		status: "stable",
 		category: "Compute & AI",
 	},
+	behaviour: {
+		suggestSkillsAfterHandler: true,
+	},
 	handler: async function handleRollback(args, { config }) {
 		const accountId = await requireAuth(config);
 		const workerName = args.name ?? config.name;
diff --git a/packages/wrangler/src/versions/secrets/bulk.ts b/packages/wrangler/src/versions/secrets/bulk.ts
index bdda6f6f43..08fefb2733 100644
--- a/packages/wrangler/src/versions/secrets/bulk.ts
+++ b/packages/wrangler/src/versions/secrets/bulk.ts
@@ -18,6 +18,7 @@ export const versionsSecretBulkCommand = createCommand({
 	behaviour: {
 		printConfigWarnings: false,
 		warnIfMultipleEnvsConfiguredButNoneSpecified: true,
+		suggestSkillsAfterHandler: true,
 	},
 	args: {
 		file: {
diff --git a/packages/wrangler/src/versions/secrets/delete.ts b/packages/wrangler/src/versions/secrets/delete.ts
index 4413b987b5..8c54fae33a 100644
--- a/packages/wrangler/src/versions/secrets/delete.ts
+++ b/packages/wrangler/src/versions/secrets/delete.ts
@@ -18,6 +18,7 @@ export const versionsSecretDeleteCommand = createCommand({
 	behaviour: {
 		printConfigWarnings: false,
 		warnIfMultipleEnvsConfiguredButNoneSpecified: true,
+		suggestSkillsAfterHandler: true,
 	},
 	args: {
 		key: {
diff --git a/packages/wrangler/src/versions/secrets/list.ts b/packages/wrangler/src/versions/secrets/list.ts
index ec5a28f97c..8b3b9d551b 100644
--- a/packages/wrangler/src/versions/secrets/list.ts
+++ b/packages/wrangler/src/versions/secrets/list.ts
@@ -16,6 +16,7 @@ export const versionsSecretsListCommand = createCommand({
 	},
 	behaviour: {
 		printConfigWarnings: false,
+		suggestSkillsAfterHandler: true,
 	},
 	args: {
 		name: {
diff --git a/packages/wrangler/src/versions/secrets/put.ts b/packages/wrangler/src/versions/secrets/put.ts
index 6dde64eb82..350a415c1e 100644
--- a/packages/wrangler/src/versions/secrets/put.ts
+++ b/packages/wrangler/src/versions/secrets/put.ts
@@ -19,6 +19,7 @@ export const versionsSecretPutCommand = createCommand({
 	behaviour: {
 		printConfigWarnings: false,
 		warnIfMultipleEnvsConfiguredButNoneSpecified: true,
+		suggestSkillsAfterHandler: true,
 	},
 	args: {
 		key: {
diff --git a/packages/wrangler/src/versions/upload.ts b/packages/wrangler/src/versions/upload.ts
index c346c810bc..7a5adae2a2 100644
--- a/packages/wrangler/src/versions/upload.ts
+++ b/packages/wrangler/src/versions/upload.ts
@@ -40,6 +40,7 @@ export const versionsUploadCommand = createCommand({
 			AUTOCREATE_RESOURCES: args.experimentalAutoCreate,
 		}),
 		warnIfMultipleEnvsConfiguredButNoneSpecified: true,
+		suggestSkillsAfterHandler: true,
 	},
 	validateArgs(args) {
 		validateDeployVersionsArgs(args, "versions upload");
diff --git a/packages/wrangler/src/versions/view.ts b/packages/wrangler/src/versions/view.ts
index 08c55097eb..2c01816211 100644
--- a/packages/wrangler/src/versions/view.ts
+++ b/packages/wrangler/src/versions/view.ts
@@ -19,6 +19,7 @@ export const versionsViewCommand = createCommand({
 	},
 	behaviour: {
 		printBanner: (args) => !args.json,
+		suggestSkillsAfterHandler: (args) => !args.json,
 	},
 	args: {
 		"version-id": {

From 7e63948f9b31fce998b4902102395629e439a8e0 Mon Sep 17 00:00:00 2001
From: =?UTF-8?q?Andr=C3=A9=20Cruz?= <acruz@cloudflare.com>
Date: Fri, 12 Jun 2026 16:33:52 +0100
Subject: [PATCH 3/4] [wrangler] add --temporary deploy fallback for
 non-interactive auth (#14042)

Co-authored-by: Sid Chatterjee <sid@cloudflare.com>
Co-authored-by: Brendan Irvine-Broque <birvine-broque@cloudflare.com>
Co-authored-by: Samuel Macleod <smacleod@cloudflare.com>
---
 .changeset/temporary-preview-accounts.md      |   8 +
 packages/workers-auth/src/auth-config-file.ts |  36 --
 packages/workers-auth/src/config-file/auth.ts |  15 +
 .../workers-auth/src/config-file/index.ts     |  16 +
 .../workers-auth/src/config-file/temporary.ts |  19 +
 packages/workers-auth/src/context.ts          |  32 +-
 packages/workers-auth/src/credentials.ts      |   2 +-
 packages/workers-auth/src/flow.ts             | 137 +++-
 packages/workers-auth/src/index.ts            |  65 +-
 packages/workers-auth/src/pow.ts              |  56 ++
 packages/workers-auth/src/state.ts            |   2 +-
 packages/workers-auth/src/temporary.ts        | 277 ++++++++
 packages/workers-auth/src/token-exchange.ts   |   2 +-
 packages/workers-auth/tests/pow.test.ts       |  57 ++
 .../wrangler/src/__tests__/d1/execute.test.ts |   4 +-
 .../src/__tests__/deploy/core.test.ts         | 609 +++++++++++++++++-
 .../experimental-commands-api.test.ts         |  98 +++
 .../__tests__/helpers/mock-upload-worker.ts   |  13 +-
 .../helpers/mock-workers-subdomain.ts         |   8 +-
 packages/wrangler/src/__tests__/index.test.ts |  25 +-
 .../wrangler/src/__tests__/logout.test.ts     |  37 ++
 packages/wrangler/src/__tests__/user.test.ts  |  44 ++
 .../versions/versions.upload.test.ts          |  73 +++
 packages/wrangler/src/cert/cert.ts            |   4 +
 .../src/core/register-yargs-command.ts        |  23 +-
 .../wrangler/src/core/temporary-commands.ts   |   7 +
 packages/wrangler/src/core/types.ts           |   9 +
 packages/wrangler/src/d1/create.ts            |   1 +
 packages/wrangler/src/d1/delete.ts            |   1 +
 packages/wrangler/src/d1/execute.ts           |   1 +
 packages/wrangler/src/d1/export.ts            |   1 +
 packages/wrangler/src/d1/info.ts              |   1 +
 packages/wrangler/src/d1/insights.ts          |   1 +
 packages/wrangler/src/d1/list.ts              |   1 +
 packages/wrangler/src/d1/migrations/apply.ts  |   1 +
 packages/wrangler/src/d1/migrations/create.ts |   1 +
 packages/wrangler/src/d1/migrations/list.ts   |   1 +
 packages/wrangler/src/d1/timeTravel/info.ts   |   1 +
 .../wrangler/src/d1/timeTravel/restore.ts     |   1 +
 packages/wrangler/src/delete.ts               |   1 +
 packages/wrangler/src/deploy/index.ts         |   1 +
 packages/wrangler/src/hyperdrive/create.ts    |   1 +
 packages/wrangler/src/hyperdrive/delete.ts    |   1 +
 packages/wrangler/src/hyperdrive/get.ts       |   1 +
 packages/wrangler/src/hyperdrive/list.ts      |   1 +
 packages/wrangler/src/hyperdrive/update.ts    |   1 +
 packages/wrangler/src/kv/index.ts             |  16 +-
 packages/wrangler/src/pages/deploy.ts         |   7 +-
 .../wrangler/src/pages/deployment-tails.ts    |   7 +-
 packages/wrangler/src/pages/deployments.ts    |  14 +-
 .../wrangler/src/pages/download-config.ts     |   7 +-
 packages/wrangler/src/pages/secret/index.ts   |   7 +-
 .../cli/commands/consumer/http-pull/add.ts    |   1 +
 .../cli/commands/consumer/http-pull/list.ts   |   1 +
 .../cli/commands/consumer/http-pull/remove.ts |   1 +
 .../src/queues/cli/commands/consumer/list.ts  |   1 +
 .../cli/commands/consumer/worker/add.ts       |   1 +
 .../cli/commands/consumer/worker/list.ts      |   1 +
 .../cli/commands/consumer/worker/remove.ts    |   1 +
 .../src/queues/cli/commands/create.ts         |   1 +
 .../src/queues/cli/commands/delete.ts         |   1 +
 .../wrangler/src/queues/cli/commands/info.ts  |   1 +
 .../wrangler/src/queues/cli/commands/list.ts  |   1 +
 .../src/queues/cli/commands/pause-resume.ts   |   2 +
 .../wrangler/src/queues/cli/commands/purge.ts |   1 +
 .../cli/commands/subscription/create.ts       |   1 +
 .../cli/commands/subscription/delete.ts       |   1 +
 .../queues/cli/commands/subscription/get.ts   |   1 +
 .../queues/cli/commands/subscription/list.ts  |   1 +
 .../cli/commands/subscription/update.ts       |   1 +
 .../src/queues/cli/commands/update.ts         |   1 +
 packages/wrangler/src/secret/index.ts         |   4 +
 packages/wrangler/src/tail/index.ts           |   1 +
 packages/wrangler/src/triggers/index.ts       |   1 +
 .../wrangler/src/user/auth-config-file.ts     |  70 +-
 .../src/user/temporary-account-path.ts        |  25 +
 packages/wrangler/src/user/temporary-terms.ts |  20 +
 packages/wrangler/src/user/user.ts            |  98 ++-
 packages/wrangler/src/versions/deploy.ts      |   1 +
 .../wrangler/src/versions/deployments/list.ts |   1 +
 .../src/versions/deployments/status.ts        |   1 +
 .../wrangler/src/versions/deployments/view.ts |   1 +
 packages/wrangler/src/versions/list.ts        |   1 +
 .../wrangler/src/versions/rollback/index.ts   |   1 +
 .../wrangler/src/versions/secrets/bulk.ts     |   1 +
 .../wrangler/src/versions/secrets/delete.ts   |   1 +
 .../wrangler/src/versions/secrets/list.ts     |   1 +
 packages/wrangler/src/versions/secrets/put.ts |   1 +
 packages/wrangler/src/versions/upload.ts      |   1 +
 packages/wrangler/src/versions/view.ts        |   1 +
 90 files changed, 1835 insertions(+), 171 deletions(-)
 create mode 100644 .changeset/temporary-preview-accounts.md
 delete mode 100644 packages/workers-auth/src/auth-config-file.ts
 create mode 100644 packages/workers-auth/src/config-file/auth.ts
 create mode 100644 packages/workers-auth/src/config-file/index.ts
 create mode 100644 packages/workers-auth/src/config-file/temporary.ts
 create mode 100644 packages/workers-auth/src/pow.ts
 create mode 100644 packages/workers-auth/src/temporary.ts
 create mode 100644 packages/workers-auth/tests/pow.test.ts
 create mode 100644 packages/wrangler/src/core/temporary-commands.ts
 create mode 100644 packages/wrangler/src/user/temporary-account-path.ts
 create mode 100644 packages/wrangler/src/user/temporary-terms.ts

diff --git a/.changeset/temporary-preview-accounts.md b/.changeset/temporary-preview-accounts.md
new file mode 100644
index 0000000000..a8778d3767
--- /dev/null
+++ b/.changeset/temporary-preview-accounts.md
@@ -0,0 +1,8 @@
+---
+"wrangler": minor
+"@cloudflare/workers-auth": minor
+---
+
+Add a `--temporary` flag that creates and uses a temporary Cloudflare preview account when you have no credentials, instead of starting the OAuth login flow.
+
+It's registered only on the commands the short-lived account token can serve — Workers (`deploy`, `versions upload`, and related commands), KV, D1, Hyperdrive, Queues, and certificate commands — and is for unauthenticated use only: passing it while already authenticated (OAuth, `CLOUDFLARE_API_TOKEN`, or a global API key) errors rather than silently ignoring the flag. Before provisioning, Wrangler handles Cloudflare's Terms of Service and Privacy Policy (interactive terminals prompt for `yes`; non-interactive shells print a notice and continue). Wrangler then runs with the short-lived token and prints a claim URL so the account can be claimed before it expires. The cached account is cleared on successful login or logout.
diff --git a/packages/workers-auth/src/auth-config-file.ts b/packages/workers-auth/src/auth-config-file.ts
deleted file mode 100644
index d83460f304..0000000000
--- a/packages/workers-auth/src/auth-config-file.ts
+++ /dev/null
@@ -1,36 +0,0 @@
-/**
- * The data that may be read from the on-disk user auth config file.
- */
-export interface UserAuthConfig {
-	oauth_token?: string;
-	refresh_token?: string;
-	expiration_time?: string;
-	scopes?: string[];
-	/** @deprecated - this field was only provided by the deprecated v1 `wrangler config` command. */
-	api_token?: string;
-}
-
-/**
- * Pluggable persistence for the user auth config.
- *
- * This package does not ship a default implementation — the consumer injects
- * one via {@link OAuthFlowContext.storage} (and into {@link getAPIToken} /
- * {@link readStoredAuthState}). Wrangler's default reads/writes a TOML file
- * under the global Wrangler config directory; other CLIs can use a different
- * location and/or serialization format (e.g. a JSONC file under a different
- * CLI's XDG config directory).
- */
-export interface AuthConfigStorage {
-	/**
-	 * Read and parse the stored auth config.
-	 * @throws if the backing store is missing or cannot be parsed. Callers treat
-	 * a throw as "not logged in via local OAuth".
-	 */
-	read(): UserAuthConfig;
-	/** Serialize and persist the auth config. */
-	write(config: UserAuthConfig): void;
-	/** Remove the backing store (used on logout). */
-	clear(): void;
-	/** Human-readable location of the backing store, for display and warnings. */
-	path(): string;
-}
diff --git a/packages/workers-auth/src/config-file/auth.ts b/packages/workers-auth/src/config-file/auth.ts
new file mode 100644
index 0000000000..2b4e7123e6
--- /dev/null
+++ b/packages/workers-auth/src/config-file/auth.ts
@@ -0,0 +1,15 @@
+import type { ConfigStorage } from ".";
+
+/**
+ * The data that may be read from the on-disk user auth config file.
+ */
+export interface UserAuthConfig {
+	oauth_token?: string;
+	refresh_token?: string;
+	expiration_time?: string;
+	scopes?: string[];
+	/** @deprecated - this field was only provided by the deprecated v1 `wrangler config` command. */
+	api_token?: string;
+}
+
+export type AuthConfigStorage = ConfigStorage<UserAuthConfig>;
diff --git a/packages/workers-auth/src/config-file/index.ts b/packages/workers-auth/src/config-file/index.ts
new file mode 100644
index 0000000000..ef48032625
--- /dev/null
+++ b/packages/workers-auth/src/config-file/index.ts
@@ -0,0 +1,16 @@
+/**
+ * Pluggable persistence for a typed config blob
+ */
+export interface ConfigStorage<T> {
+	/**
+	 * Read and parse the stored config.
+	 * @throws if the backing store is missing or cannot be parsed.
+	 */
+	read(): T;
+	/** Serialize and persist the config. */
+	write(config: T): void;
+	/** Remove the backing store; returns whether anything existed beforehand. */
+	clear(): boolean;
+	/** Human-readable location of the backing store, for display and warnings. */
+	path(): string;
+}
diff --git a/packages/workers-auth/src/config-file/temporary.ts b/packages/workers-auth/src/config-file/temporary.ts
new file mode 100644
index 0000000000..880ca2edd8
--- /dev/null
+++ b/packages/workers-auth/src/config-file/temporary.ts
@@ -0,0 +1,19 @@
+import type { ConfigStorage } from ".";
+
+/**
+ * A short-lived "temporary preview account"
+ */
+export type TemporaryPreviewAccount = {
+	account: {
+		id: string;
+		name: string;
+		apiToken: string;
+		expiresAt: string;
+	};
+	claim: {
+		url: string;
+		expiresAt: string;
+	};
+};
+
+export type TemporaryAccountStorage = ConfigStorage<TemporaryPreviewAccount>;
diff --git a/packages/workers-auth/src/context.ts b/packages/workers-auth/src/context.ts
index b1c66348b1..f581a47e67 100644
--- a/packages/workers-auth/src/context.ts
+++ b/packages/workers-auth/src/context.ts
@@ -1,7 +1,25 @@
-import type { AuthConfigStorage } from "./auth-config-file";
+import type { AuthConfigStorage } from "./config-file/auth";
+import type { TemporaryAccountStorage } from "./config-file/temporary";
 import type { generateAuthUrl as defaultGenerateAuthUrl } from "./generate-auth-url";
 import type { generateRandomState as defaultGenerateRandomState } from "./generate-random-state";
 
+/**
+ * The dependencies the OAuth flow needs to mint/reuse a short-lived "temporary
+ * preview account"
+ */
+export interface OAuthFlowTemporaryContext {
+	/** Persistence backend for the cached temporary preview account. */
+	storage: TemporaryAccountStorage;
+	/**
+	 * Hook to customise the terms-acceptance interactive prompt
+	 *  - question: the question to ask a user in interactive mode.
+	 *    return answer === "yes" (must be the literal string)
+	 *  - notice: the notice to print on stderr if in non-interactive mode
+	 *    always return true
+	 */
+	prompt: (question: string, notice: string) => Promise<boolean>;
+}
+
 /**
  * The branded OAuth consent pages the provider redirects the browser to after
  * the user grants or denies consent.
@@ -90,6 +108,18 @@ export interface OAuthFlowContext {
 	 */
 	storage: AuthConfigStorage;
 
+	/**
+	 * Whether the flow's credential resolvers (`getAPIToken` / `requireApiToken`)
+	 * should honour the global API key + email pair in addition to scoped API
+	 * tokens.
+	 */
+	allowGlobalAuthKey: boolean;
+
+	/**
+	 * Dependencies for minting/reusing a temporary preview account.
+	 */
+	temporary: OAuthFlowTemporaryContext | undefined;
+
 	/**
 	 * Override the OAuth authorize URL generator. Used by tests to produce a
 	 * deterministic URL for snapshot testing. Defaults to the standard
diff --git a/packages/workers-auth/src/credentials.ts b/packages/workers-auth/src/credentials.ts
index 79efa25c22..b90912a099 100644
--- a/packages/workers-auth/src/credentials.ts
+++ b/packages/workers-auth/src/credentials.ts
@@ -2,8 +2,8 @@ import {
 	getEnvironmentVariableFactory,
 	UserError,
 } from "@cloudflare/workers-utils";
-import { type AuthConfigStorage } from "./auth-config-file";
 import { readStoredAuthState } from "./state";
+import type { AuthConfigStorage } from "./config-file/auth";
 import type { OAuthFlowLogger } from "./context";
 import type { ApiCredentials } from "@cloudflare/workers-utils";
 
diff --git a/packages/workers-auth/src/flow.ts b/packages/workers-auth/src/flow.ts
index 2336920415..ed8d3901e9 100644
--- a/packages/workers-auth/src/flow.ts
+++ b/packages/workers-auth/src/flow.ts
@@ -19,13 +19,19 @@ import {
 import dedent from "ts-dedent";
 import { fetch } from "undici";
 import { getOauthToken } from "./callback-server";
+import { getAPIToken, requireApiToken } from "./credentials";
 import { getRevokeUrlFromEnv } from "./env-vars";
 import { generateAuthUrl as defaultGenerateAuthUrl } from "./generate-auth-url";
 import { generateRandomState as defaultGenerateRandomState } from "./generate-random-state";
 import { readStoredAuthState, type OAuthFlowState } from "./state";
+import { getOrCreateTemporaryPreviewAccount } from "./temporary";
 import { exchangeRefreshTokenForAccessToken } from "./token-exchange";
+import type { TemporaryPreviewAccount } from "./config-file/temporary";
 import type { OAuthFlowContext } from "./context";
-import type { ComplianceConfig } from "@cloudflare/workers-utils";
+import type {
+	ApiCredentials,
+	ComplianceConfig,
+} from "@cloudflare/workers-utils";
 
 /**
  * Reason why {@link OAuthFlowAPI.loginOrRefreshIfRequired} could not
@@ -124,18 +130,50 @@ export interface OAuthFlowAPI {
 	getOAuthTokenFromLocalState(): Promise<string | undefined>;
 
 	/**
-	 * Whether the stored OAuth access token has expired and a refresh is
-	 * required before it can be used. Returns `false` when env credentials are
-	 * present (per `ctx.hasEnvCredentials`), because the stored OAuth state is
-	 * not consulted in that case.
+	 * Resolve API credentials, preferring an active temporary preview account
+	 * (when one has been latched via {@link activateTemporaryAccount}) over the
+	 * env / stored-OAuth resolution performed by the shared credential resolver.
+	 *
+	 * Returns `undefined` when no credentials are available.
+	 */
+	getAPIToken(): ApiCredentials | undefined;
+
+	/**
+	 * Like {@link getAPIToken}, but throws a `UserError` when no credentials are
+	 * available.
+	 */
+	requireApiToken(): ApiCredentials;
+
+	/**
+	 * Establish whether `--temporary` is permitted for this invocation. Called
+	 * once at command dispatch by the consumer. Also drops any temporary account
+	 * latched by a previous dispatch, so that — when multiple commands share a
+	 * process (e.g. in tests) — each invocation starts a fresh temporary session.
+	 * No-op when the flow was created without a `temporary` context.
+	 */
+	setTemporaryAllowed(allowed: boolean): void;
+
+	/**
+	 * Whether `--temporary` is permitted for this invocation (see
+	 * {@link setTemporaryAllowed}). Always `false` without a `temporary` context.
+	 */
+	isTemporaryAllowed(): boolean;
+
+	/**
+	 * The temporary preview account latched for this invocation, or `undefined`.
+	 * Only set after {@link activateTemporaryAccount} has run.
 	 */
-	isRefreshNeeded(): boolean;
+	getActiveTemporaryAccount(): TemporaryPreviewAccount | undefined;
 
 	/**
-	 * Trigger an OAuth refresh-token rotation. Persists the new access/refresh
-	 * tokens to disk on success. Returns `false` on any failure.
+	 * The sole creator of the temporary-account latch: mint a fresh temporary
+	 * preview account (or reuse a cached one), latch it for this invocation, and
+	 * return it. Requires a `temporary` context.
 	 */
-	refreshToken(): Promise<boolean>;
+	activateTemporaryAccount(): Promise<{
+		account: TemporaryPreviewAccount;
+		cached: boolean;
+	}>;
 }
 
 /**
@@ -157,6 +195,9 @@ export function createOAuthFlow(ctx: OAuthFlowContext): OAuthFlowAPI {
 		typeof ctx.clientId === "function" ? ctx.clientId() : ctx.clientId;
 	const consent = ctx.consent;
 
+	let temporaryAllowed = false;
+	let activeTemporaryAccount: TemporaryPreviewAccount | undefined;
+
 	const redirectUrl = new URL(ctx.redirectUri);
 	const defaultCallbackHost = redirectUrl.hostname;
 	const defaultCallbackPort = Number(redirectUrl.port);
@@ -217,6 +258,7 @@ export function createOAuthFlow(ctx: OAuthFlowContext): OAuthFlowAPI {
 
 		ctx.logger.log(`Successfully logged in.`);
 
+		clearTemporaryAccount();
 		ctx.purgeOnLoginOrLogout?.();
 
 		return true;
@@ -321,6 +363,8 @@ export function createOAuthFlow(ctx: OAuthFlowContext): OAuthFlowAPI {
 	}
 
 	async function logout(): Promise<void> {
+		const clearedTemporary = clearTemporaryAccount();
+
 		if (ctx.hasEnvCredentials()) {
 			// Env credentials override any login details, so we cannot log out.
 			ctx.logger.log(
@@ -335,7 +379,11 @@ export function createOAuthFlow(ctx: OAuthFlowContext): OAuthFlowAPI {
 			storage,
 		}).refreshToken;
 		if (!storedRefreshToken) {
-			ctx.logger.log("Not logged in, exiting...");
+			ctx.logger.log(
+				clearedTemporary
+					? "Cleared temporary preview account."
+					: "Not logged in, exiting..."
+			);
 			return;
 		}
 
@@ -383,12 +431,77 @@ export function createOAuthFlow(ctx: OAuthFlowContext): OAuthFlowAPI {
 		return stored.accessToken?.value;
 	}
 
+	function getAPITokenInternal(): ApiCredentials | undefined {
+		if (activeTemporaryAccount) {
+			return { apiToken: activeTemporaryAccount.account.apiToken };
+		}
+
+		return getAPIToken({
+			storage,
+			warningLogger: ctx.logger,
+			allowGlobalAuthKey: ctx.allowGlobalAuthKey,
+		});
+	}
+
+	function requireApiTokenInternal(): ApiCredentials {
+		if (activeTemporaryAccount) {
+			return { apiToken: activeTemporaryAccount.account.apiToken };
+		}
+
+		return requireApiToken({
+			storage,
+			warningLogger: ctx.logger,
+			allowGlobalAuthKey: ctx.allowGlobalAuthKey,
+		});
+	}
+
+	function setTemporaryAllowed(allowed: boolean): void {
+		temporaryAllowed = allowed && ctx.temporary !== undefined;
+		activeTemporaryAccount = undefined;
+	}
+
+	function isTemporaryAllowed(): boolean {
+		return temporaryAllowed;
+	}
+
+	function getActiveTemporaryAccount(): TemporaryPreviewAccount | undefined {
+		return activeTemporaryAccount;
+	}
+
+	async function activateTemporaryAccount(): Promise<{
+		account: TemporaryPreviewAccount;
+		cached: boolean;
+	}> {
+		if (!ctx.temporary) {
+			throw new UserError(
+				"Temporary preview accounts are not supported by this CLI.",
+				{ telemetryMessage: "user temporary account unsupported" }
+			);
+		}
+
+		const result = await getOrCreateTemporaryPreviewAccount({
+			...ctx.temporary,
+			logger: ctx.logger,
+		});
+		activeTemporaryAccount = result.account;
+		return result;
+	}
+
+	function clearTemporaryAccount(): boolean {
+		activeTemporaryAccount = undefined;
+		return ctx.temporary?.storage.clear() ?? false;
+	}
+
 	return {
 		login,
 		logout,
 		loginOrRefreshIfRequired,
 		getOAuthTokenFromLocalState,
-		isRefreshNeeded,
-		refreshToken,
+		getAPIToken: getAPITokenInternal,
+		requireApiToken: requireApiTokenInternal,
+		setTemporaryAllowed,
+		isTemporaryAllowed,
+		getActiveTemporaryAccount,
+		activateTemporaryAccount,
 	};
 }
diff --git a/packages/workers-auth/src/index.ts b/packages/workers-auth/src/index.ts
index 1a5d5055cb..b4a480e906 100644
--- a/packages/workers-auth/src/index.ts
+++ b/packages/workers-auth/src/index.ts
@@ -6,88 +6,37 @@
 // `getAPIToken` resolver), or to inject deterministic implementations into
 // tests.
 
-export type { AuthConfigStorage, UserAuthConfig } from "./auth-config-file";
+export type { ConfigStorage } from "./config-file";
 
+export type { AuthConfigStorage, UserAuthConfig } from "./config-file/auth";
 export {
-	getAPIToken,
 	getAuthFromEnv,
 	getCloudflareAPITokenFromEnv,
 	getCloudflareGlobalAuthEmailFromEnv,
 	getCloudflareGlobalAuthKeyFromEnv,
-	requireApiToken,
 } from "./credentials";
-export type { GetAPITokenOptions, GetAuthFromEnvOptions } from "./credentials";
 
 export {
 	clearAccessCaches,
 	domainUsesAccess,
 	getAccessHeaders,
-	getCloudflareAccessHeaders,
 } from "./access";
 
-export type {
-	OAuthConsentPages,
-	OAuthFlowContext,
-	OAuthFlowLogger,
-} from "./context";
-
-export {
-	getAccessClientIdFromEnv,
-	getAccessClientSecretFromEnv,
-	getAuthDomainFromEnv,
-	getAuthUrlFromEnv,
-	getCfAuthorizationTokenFromEnv,
-	getRevokeUrlFromEnv,
-	getTokenUrlFromEnv,
-} from "./env-vars";
-
-export {
-	ErrorAccessDenied,
-	ErrorAccessTokenResponse,
-	ErrorAuthenticationGrant,
-	ErrorInvalidClient,
-	ErrorInvalidGrant,
-	ErrorInvalidJson,
-	ErrorInvalidRequest,
-	ErrorInvalidReturnedStateParam,
-	ErrorInvalidScope,
-	ErrorInvalidToken,
-	ErrorNoAuthCode,
-	ErrorOAuth2,
-	ErrorServerError,
-	ErrorTemporarilyUnavailable,
-	ErrorUnauthorizedClient,
-	ErrorUnknown,
-	ErrorUnsupportedGrantType,
-	ErrorUnsupportedResponseType,
-	toErrorClass,
-} from "./errors";
+export { getAuthUrlFromEnv } from "./env-vars";
 
 export { createOAuthFlow } from "./flow";
 export type {
 	LoginOrRefreshFailureReason,
 	LoginOrRefreshResult,
 	LoginProps,
-	OAuthFlowAPI,
 } from "./flow";
 
 export { generateAuthUrl } from "./generate-auth-url";
 
 export { generateRandomState } from "./generate-random-state";
-
-export {
-	base64urlEncode,
-	generatePKCECodes,
-	PKCE_CHARSET,
-	RECOMMENDED_CODE_VERIFIER_LENGTH,
-	RECOMMENDED_STATE_LENGTH,
-} from "./pkce";
-export type { PKCECodes } from "./pkce";
+export { TEMPORARY_TERMS_NOTICE, TEMPORARY_TERMS_PROMPT } from "./temporary";
+export { PKCE_CHARSET } from "./pkce";
 
 export { readStoredAuthState } from "./state";
-export type {
-	AccessToken,
-	OAuthFlowState,
-	RefreshToken,
-	StoredAuthState,
-} from "./state";
+
+export type { TemporaryPreviewAccount } from "./config-file/temporary";
diff --git a/packages/workers-auth/src/pow.ts b/packages/workers-auth/src/pow.ts
new file mode 100644
index 0000000000..f0b45f8169
--- /dev/null
+++ b/packages/workers-auth/src/pow.ts
@@ -0,0 +1,56 @@
+import { createHash } from "node:crypto";
+
+export const POW_PROTOCOL_VERSION = 1;
+
+// Upper bound on the total work (k*g hashes) we'll solve. Solve time is
+// proportional to k*g, so bounding the product caps it regardless of how the
+// server splits difficulty. The provisioning service tops out around k=8000,
+// g=2000 (16M); this leaves headroom for a legitimate server-side bump while
+// still bounding a buggy or hostile challenge to a finite solve.
+export const POW_MAX_ITERATIONS = 64_000_000;
+
+export interface PowChallenge {
+	challengeToken: string;
+	seed: string;
+	k: number;
+	g: number;
+}
+
+export interface PowSolution {
+	challengeToken: string;
+	solution: { checkpoints: string };
+}
+
+// Sequential SHA-256 chain (spec §5.2): h0 = SHA256(seed), then k segments of g
+// hashes, recording a checkpoint at each segment boundary. Inherently
+// sequential, so it can't be parallelised.
+function solvePow(seed: Buffer, k: number, g: number): Buffer[] {
+	const checkpoints: Buffer[] = new Array(k + 1);
+	let h = createHash("sha256").update(seed).digest();
+	checkpoints[0] = h;
+	for (let j = 0; j < k; j++) {
+		for (let i = 0; i < g; i++) {
+			h = createHash("sha256").update(h).digest();
+		}
+		checkpoints[j + 1] = h;
+	}
+	return checkpoints;
+}
+
+// Standard base64 of the concatenated (k+1)*32 bytes, matching the worker
+// verifier's decode.
+function encodeCheckpoints(checkpoints: Buffer[]): string {
+	return Buffer.concat(checkpoints).toString("base64");
+}
+
+export function solveChallenge(challenge: PowChallenge): PowSolution {
+	const checkpoints = solvePow(
+		Buffer.from(challenge.seed, "base64url"),
+		challenge.k,
+		challenge.g
+	);
+	return {
+		challengeToken: challenge.challengeToken,
+		solution: { checkpoints: encodeCheckpoints(checkpoints) },
+	};
+}
diff --git a/packages/workers-auth/src/state.ts b/packages/workers-auth/src/state.ts
index 8d1c5e7225..e3b4011619 100644
--- a/packages/workers-auth/src/state.ts
+++ b/packages/workers-auth/src/state.ts
@@ -1,4 +1,4 @@
-import type { AuthConfigStorage, UserAuthConfig } from "./auth-config-file";
+import type { AuthConfigStorage, UserAuthConfig } from "./config-file/auth";
 import type { OAuthFlowLogger } from "./context";
 
 export interface RefreshToken {
diff --git a/packages/workers-auth/src/temporary.ts b/packages/workers-auth/src/temporary.ts
new file mode 100644
index 0000000000..169cff6964
--- /dev/null
+++ b/packages/workers-auth/src/temporary.ts
@@ -0,0 +1,277 @@
+import {
+	COMPLIANCE_REGION_CONFIG_PUBLIC,
+	FatalError,
+	getCloudflareApiBaseUrl,
+	UserError,
+} from "@cloudflare/workers-utils";
+import { fetch } from "undici";
+import { POW_MAX_ITERATIONS, solveChallenge } from "./pow";
+import type {
+	TemporaryAccountStorage,
+	TemporaryPreviewAccount,
+} from "./config-file/temporary";
+import type { OAuthFlowLogger } from "./context";
+import type { PowSolution } from "./pow";
+
+export const TEMPORARY_TERMS_URLS = {
+	termsOfService: "https://www.cloudflare.com/terms/",
+	privacyPolicy: "https://www.cloudflare.com/privacypolicy/",
+} as const;
+
+export const TEMPORARY_TERMS_PROMPT = `You must accept Cloudflare's Terms of Service (${TEMPORARY_TERMS_URLS.termsOfService}) and Privacy Policy (${TEMPORARY_TERMS_URLS.privacyPolicy}) in order to continue. By typing "yes", you agree to these terms. Type "yes" to continue.`;
+export const TEMPORARY_TERMS_NOTICE = `Continuing means you accept Cloudflare's Terms of Service (${TEMPORARY_TERMS_URLS.termsOfService}) and Privacy Policy (${TEMPORARY_TERMS_URLS.privacyPolicy}).`;
+
+const TEMPORARY_TERMS_ERROR = `You must accept Cloudflare's Terms of Service (${TEMPORARY_TERMS_URLS.termsOfService}) and Privacy Policy (${TEMPORARY_TERMS_URLS.privacyPolicy}) to use --temporary.`;
+
+type TemporaryAccountPayload = {
+	account?: {
+		id?: string;
+		name?: string;
+		type?: string;
+		apiToken?: string;
+		tokenId?: string;
+		expiresAt?: string;
+	};
+	claim?: {
+		token?: string;
+		url?: string;
+		expiresAt?: string;
+	};
+};
+
+type TemporaryAccountResponse = {
+	result?: TemporaryAccountPayload;
+};
+
+function getTemporaryPreviewUrl(): string {
+	return `${getCloudflareApiBaseUrl(COMPLIANCE_REGION_CONFIG_PUBLIC)}/provisioning/previews`;
+}
+
+function getTemporaryPreviewChallengeUrl(): string {
+	return `${getTemporaryPreviewUrl()}/challenge`;
+}
+
+function isFutureTimestamp(timestamp: string): boolean {
+	const parsed = Date.parse(timestamp);
+	return !Number.isNaN(parsed) && parsed > Date.now();
+}
+
+/**
+ * Read the cached temporary preview account from the injected storage,
+ * validating that it has all required fields and that neither the account nor
+ * the claim has expired. Returns `undefined` when there is no usable cache.
+ */
+export function getCachedTemporaryPreviewAccount(
+	storage: TemporaryAccountStorage
+): TemporaryPreviewAccount | undefined {
+	let temporaryPreviewAccount: TemporaryPreviewAccount | undefined;
+	try {
+		temporaryPreviewAccount = storage.read();
+	} catch {
+		return undefined;
+	}
+
+	if (!temporaryPreviewAccount) {
+		return undefined;
+	}
+
+	if (
+		!temporaryPreviewAccount.account?.id ||
+		!temporaryPreviewAccount.account?.apiToken ||
+		!temporaryPreviewAccount.account?.name ||
+		!temporaryPreviewAccount.claim?.url ||
+		!isFutureTimestamp(temporaryPreviewAccount.account?.expiresAt ?? "") ||
+		!isFutureTimestamp(temporaryPreviewAccount.claim?.expiresAt ?? "")
+	) {
+		return undefined;
+	}
+
+	return temporaryPreviewAccount;
+}
+
+type PowChallengeResponse = {
+	result?: {
+		challengeToken?: string;
+		seed?: string;
+		k?: number;
+		g?: number;
+	};
+};
+
+// Requests a proof-of-work challenge and solves it. The challenge is required:
+// any failure aborts provisioning.
+async function requestPowSolution(
+	logger: OAuthFlowLogger
+): Promise<PowSolution> {
+	const response = await fetch(getTemporaryPreviewChallengeUrl(), {
+		method: "POST",
+		headers: { "Content-Type": "application/json" },
+		body: "{}",
+	});
+
+	if (!response.ok) {
+		throw new FatalError(
+			`Failed to request a proof-of-work challenge (${response.status} ${response.statusText}).`,
+			{ telemetryMessage: "deploy temporary account challenge failed" }
+		);
+	}
+
+	let body: PowChallengeResponse;
+	try {
+		body = (await response.json()) as PowChallengeResponse;
+	} catch {
+		throw new FatalError(
+			`Failed to request a proof-of-work challenge. Received an invalid response (${response.status} ${response.statusText}).`,
+			{
+				telemetryMessage: "deploy temporary account challenge invalid response",
+			}
+		);
+	}
+
+	const { challengeToken, seed, k, g } = body.result ?? {};
+	if (
+		challengeToken === undefined ||
+		seed === undefined ||
+		k === undefined ||
+		g === undefined
+	) {
+		throw new FatalError(
+			"Failed to request a proof-of-work challenge because the response was missing required fields.",
+			{ telemetryMessage: "deploy temporary account challenge incomplete" }
+		);
+	}
+
+	if (
+		!Number.isInteger(k) ||
+		!Number.isInteger(g) ||
+		k <= 0 ||
+		g <= 0 ||
+		k * g > POW_MAX_ITERATIONS ||
+		Buffer.from(seed, "base64url").length !== 32
+	) {
+		throw new FatalError(
+			"The proof-of-work challenge is not supported by this version of Wrangler.",
+			{
+				telemetryMessage:
+					"deploy temporary account challenge difficulty unsupported",
+			}
+		);
+	}
+
+	logger.log("Solving proof-of-work challenge…");
+	return solveChallenge({ challengeToken, seed, k, g });
+}
+
+/**
+ * Provision a brand new temporary preview account from the public provisioning
+ * endpoint
+ */
+export async function createTemporaryPreviewAccount(
+	logger: OAuthFlowLogger
+): Promise<TemporaryPreviewAccount> {
+	const pow = await requestPowSolution(logger);
+
+	const response = await fetch(getTemporaryPreviewUrl(), {
+		method: "POST",
+		headers: { "Content-Type": "application/json" },
+		body: JSON.stringify({
+			termsOfService: TEMPORARY_TERMS_URLS.termsOfService,
+			privacyPolicy: TEMPORARY_TERMS_URLS.privacyPolicy,
+			acceptTermsOfService: "yes",
+			challengeToken: pow.challengeToken,
+			solution: pow.solution,
+		}),
+	});
+
+	if (!response.ok) {
+		throw new FatalError(
+			`Failed to create a temporary preview account (${response.status} ${response.statusText}).`,
+			{ telemetryMessage: "deploy temporary account create failed" }
+		);
+	}
+
+	let responseBody: TemporaryAccountResponse;
+
+	try {
+		responseBody = (await response.json()) as TemporaryAccountResponse;
+	} catch {
+		throw new FatalError(
+			`Failed to create a temporary preview account. Received an invalid response (${response.status} ${response.statusText}).`,
+			{ telemetryMessage: "deploy temporary account invalid response" }
+		);
+	}
+
+	const previewAccount = responseBody.result;
+	const accountId = previewAccount?.account?.id;
+	const accountName = previewAccount?.account?.name;
+	const apiToken = previewAccount?.account?.apiToken;
+	const accountExpiresAt = previewAccount?.account?.expiresAt;
+	const claimUrl = previewAccount?.claim?.url;
+	const claimExpiresAt = previewAccount?.claim?.expiresAt;
+
+	if (
+		accountId === undefined ||
+		accountName === undefined ||
+		apiToken === undefined ||
+		accountExpiresAt === undefined ||
+		claimUrl === undefined ||
+		claimExpiresAt === undefined
+	) {
+		throw new FatalError(
+			"Failed to create a temporary preview account because the response was missing required fields.",
+			{ telemetryMessage: "deploy temporary account response incomplete" }
+		);
+	}
+
+	return {
+		account: {
+			id: accountId,
+			name: accountName,
+			apiToken,
+			expiresAt: accountExpiresAt,
+		},
+		claim: {
+			url: claimUrl,
+			expiresAt: claimExpiresAt,
+		},
+	};
+}
+
+/**
+ * Return the cached temporary preview account if one is still valid, otherwise
+ * mint a fresh one (running `beforeCreate` first, e.g. a terms-acceptance gate)
+ * and persist it to the injected storage.
+ */
+export async function getOrCreateTemporaryPreviewAccount(options: {
+	storage: TemporaryAccountStorage;
+	prompt: (question: string, notice: string) => Promise<boolean>;
+	logger: OAuthFlowLogger;
+}): Promise<{
+	account: TemporaryPreviewAccount;
+	cached: boolean;
+}> {
+	const cachedPreviewAccount = getCachedTemporaryPreviewAccount(
+		options.storage
+	);
+	if (cachedPreviewAccount) {
+		return { account: cachedPreviewAccount, cached: true };
+	}
+
+	const termsAccepted = await options.prompt(
+		TEMPORARY_TERMS_PROMPT,
+		TEMPORARY_TERMS_NOTICE
+	);
+
+	if (!termsAccepted) {
+		throw new UserError(TEMPORARY_TERMS_ERROR, {
+			telemetryMessage: "user temporary terms not accepted",
+		});
+	}
+
+	const temporaryPreviewAccount = await createTemporaryPreviewAccount(
+		options.logger
+	);
+	options.storage.write(temporaryPreviewAccount);
+
+	return { account: temporaryPreviewAccount, cached: false };
+}
diff --git a/packages/workers-auth/src/token-exchange.ts b/packages/workers-auth/src/token-exchange.ts
index 1521ac3b1a..ef703a1581 100644
--- a/packages/workers-auth/src/token-exchange.ts
+++ b/packages/workers-auth/src/token-exchange.ts
@@ -27,7 +27,7 @@ import {
 } from "./errors";
 import { generatePKCECodes, RECOMMENDED_STATE_LENGTH } from "./pkce";
 import { readStoredAuthState, type OAuthFlowState } from "./state";
-import type { AuthConfigStorage } from "./auth-config-file";
+import type { AuthConfigStorage } from "./config-file/auth";
 import type { OAuthFlowContext } from "./context";
 import type { generateAuthUrl as defaultGenerateAuthUrl } from "./generate-auth-url";
 import type { generateRandomState as defaultGenerateRandomState } from "./generate-random-state";
diff --git a/packages/workers-auth/tests/pow.test.ts b/packages/workers-auth/tests/pow.test.ts
new file mode 100644
index 0000000000..29475c378d
--- /dev/null
+++ b/packages/workers-auth/tests/pow.test.ts
@@ -0,0 +1,57 @@
+import { createHash } from "node:crypto";
+import { describe, it } from "vitest";
+import { solveChallenge } from "../src/pow";
+
+const CHECKPOINT_BYTES = 32;
+
+function sha256(input: Buffer): Buffer {
+	return createHash("sha256").update(input).digest();
+}
+
+describe("proof-of-work solver", () => {
+	it("produces a contiguous checkpoint ladder anchored at the seed", ({
+		expect,
+	}) => {
+		const seed = Buffer.alloc(32, 7);
+		const k = 4;
+		const g = 5;
+
+		const { solution } = solveChallenge({
+			challengeToken: "token",
+			seed: seed.toString("base64url"),
+			k,
+			g,
+		});
+
+		const flat = Buffer.from(solution.checkpoints, "base64");
+		expect(flat.length).toBe((k + 1) * CHECKPOINT_BYTES);
+
+		const checkpoints: Buffer[] = [];
+		for (let i = 0; i <= k; i++) {
+			checkpoints.push(
+				flat.subarray(i * CHECKPOINT_BYTES, (i + 1) * CHECKPOINT_BYTES)
+			);
+		}
+
+		// C[0] == SHA256(seed), and each segment chains g hashes into the next
+		// checkpoint — the same relation the worker verifier spot-checks.
+		expect(checkpoints[0].equals(sha256(seed))).toBe(true);
+		for (let j = 0; j < k; j++) {
+			let h = checkpoints[j];
+			for (let i = 0; i < g; i++) {
+				h = sha256(h);
+			}
+			expect(h.equals(checkpoints[j + 1])).toBe(true);
+		}
+	});
+
+	it("passes the challenge token through unchanged", ({ expect }) => {
+		const { challengeToken } = solveChallenge({
+			challengeToken: "abc.def",
+			seed: Buffer.alloc(32).toString("base64url"),
+			k: 1,
+			g: 1,
+		});
+		expect(challengeToken).toBe("abc.def");
+	});
+});
diff --git a/packages/wrangler/src/__tests__/d1/execute.test.ts b/packages/wrangler/src/__tests__/d1/execute.test.ts
index 5713aaffaf..3eb7080ec7 100644
--- a/packages/wrangler/src/__tests__/d1/execute.test.ts
+++ b/packages/wrangler/src/__tests__/d1/execute.test.ts
@@ -33,7 +33,9 @@ describe("execute", () => {
 		await expect(
 			runWrangler("d1 execute db --command 'select 1;' --remote")
 		).rejects.toThrowError(
-			`In a non-interactive environment, it's necessary to set a CLOUDFLARE_API_TOKEN environment variable for wrangler to work. Please go to https://developers.cloudflare.com/fundamentals/api/get-started/create-token/ for instructions on how to create an api token, and assign its value to CLOUDFLARE_API_TOKEN.`
+			`In a non-interactive environment, it's necessary to set a CLOUDFLARE_API_TOKEN environment variable for wrangler to work. Please go to https://developers.cloudflare.com/fundamentals/api/get-started/create-token/ for instructions on how to create an api token, and assign its value to CLOUDFLARE_API_TOKEN.
+
+To continue without logging in, rerun this command with \`--temporary\`. Wrangler will use a temporary account and print a claim URL.`
 		);
 	});
 
diff --git a/packages/wrangler/src/__tests__/deploy/core.test.ts b/packages/wrangler/src/__tests__/deploy/core.test.ts
index a599b7f9c7..589cd3d661 100644
--- a/packages/wrangler/src/__tests__/deploy/core.test.ts
+++ b/packages/wrangler/src/__tests__/deploy/core.test.ts
@@ -1,6 +1,11 @@
 import * as fs from "node:fs";
 import { readFile } from "node:fs/promises";
 import * as path from "node:path";
+import {
+	TEMPORARY_TERMS_NOTICE,
+	TEMPORARY_TERMS_PROMPT,
+} from "@cloudflare/workers-auth";
+import { getGlobalWranglerConfigPath } from "@cloudflare/workers-utils";
 import {
 	runInTempDir,
 	writeWranglerConfig,
@@ -19,7 +24,7 @@ import { writeAuthConfigFile } from "../../user";
 import { mockAccountId, mockApiToken } from "../helpers/mock-account-id";
 import { mockAuthDomain } from "../helpers/mock-auth-domain";
 import { mockConsoleMethods } from "../helpers/mock-console";
-import { clearDialogs, mockConfirm } from "../helpers/mock-dialogs";
+import { clearDialogs, mockConfirm, mockPrompt } from "../helpers/mock-dialogs";
 import { useMockIsTTY } from "../helpers/mock-istty";
 import {
 	mockExchangeRefreshTokenForAccessToken,
@@ -89,6 +94,32 @@ describe("deploy", () => {
 		mockGrantAccessToken,
 		mockDomainUsesAccess,
 	} = mockOAuthFlow();
+	const temporaryPreviewAccountUrl =
+		"https://api.cloudflare.com/client/v4/provisioning/previews";
+
+	// Mocks the proof-of-work challenge minting expects. Small k/g so the
+	// solve is instant.
+	function mockTemporaryPreviewChallenge(
+		url = `${temporaryPreviewAccountUrl}/challenge`
+	) {
+		msw.use(
+			http.post(url, () =>
+				HttpResponse.json({
+					success: true,
+					result: {
+						challengeToken: "challenge-token",
+						seed: Buffer.alloc(32, 1).toString("base64url"),
+						k: 2,
+						g: 2,
+						s: 16,
+						expiresAt: 9999999999,
+					},
+					errors: [],
+					messages: [],
+				})
+			)
+		);
+	}
 
 	beforeEach(() => {
 		vi.stubGlobal("setTimeout", (fn: () => void) => {
@@ -774,6 +805,95 @@ describe("deploy", () => {
 			expect(std.err).toMatchInlineSnapshot(`""`);
 		});
 
+		it("creates a temporary preview account in interactive mode when --temporary is passed", async ({
+			expect,
+		}) => {
+			setIsTTY(true);
+			mockPrompt({ text: TEMPORARY_TERMS_PROMPT, result: "yes" });
+			writeWranglerConfig();
+			writeWorkerSource();
+			mockSubDomainRequest("test-sub-domain", true, false);
+			mockUploadWorkerRequest({
+				expectedAccountId: "preview-account-id",
+			});
+
+			let previewAccountRequests = 0;
+			let contentTypeHeader: string | null = null;
+			mockTemporaryPreviewChallenge();
+			msw.use(
+				http.get(
+					"*/accounts/preview-account-id/workers/services/:scriptName",
+					() => {
+						return HttpResponse.json(
+							createFetchResult({
+								default_environment: {
+									script: { last_deployed_from: "wrangler" },
+								},
+							})
+						);
+					}
+				),
+				http.post(temporaryPreviewAccountUrl, async ({ request }) => {
+					previewAccountRequests += 1;
+					contentTypeHeader = request.headers.get("Content-Type");
+					return HttpResponse.json({
+						success: true,
+						result: {
+							account: {
+								id: "preview-account-id",
+								name: "Preview Account Alpha",
+								type: "standard",
+								apiToken: "preview-account-token",
+								tokenId: "preview-token-id",
+								expiresAt: "2027-01-01T00:00:00.000Z",
+							},
+							claim: {
+								token: "claim-token",
+								url: "https://dash.cloudflare.com/claim-preview?claimToken=claim-token",
+								expiresAt: "2027-01-02T00:00:00.000Z",
+							},
+						},
+						errors: [],
+						messages: [],
+					});
+				})
+			);
+
+			await expect(
+				runWrangler("deploy index.js --temporary")
+			).resolves.toBeUndefined();
+
+			expect(previewAccountRequests).toBe(1);
+			expect(contentTypeHeader).toBe("application/json");
+			expect(std.out).not.toContain("Attempting to login via OAuth...");
+			expect(std.out).toContain("Temporary account ready:");
+		});
+
+		it("aborts in interactive mode when the terms are not accepted", async ({
+			expect,
+		}) => {
+			setIsTTY(true);
+			mockPrompt({ text: TEMPORARY_TERMS_PROMPT, result: "no" });
+			writeWranglerConfig();
+			writeWorkerSource();
+
+			let previewAccountRequests = 0;
+			msw.use(
+				http.post(temporaryPreviewAccountUrl, async () => {
+					previewAccountRequests += 1;
+					return HttpResponse.json({});
+				})
+			);
+
+			await expect(
+				runWrangler("deploy index.js --temporary")
+			).rejects.toThrowError(
+				/You must accept Cloudflare's Terms of Service .* to use --temporary\./
+			);
+
+			expect(previewAccountRequests).toBe(0);
+		});
+
 		describe("with an alternative auth domain", () => {
 			mockAuthDomain({ domain: "dash.staging.cloudflare.com" });
 
@@ -863,7 +983,424 @@ describe("deploy", () => {
 			expect(std.err).toMatchInlineSnapshot(`""`);
 		});
 
-		describe("non-TTY", () => {
+		it("throws when the user is already authenticated and requests a temporary account", async ({
+			expect,
+		}) => {
+			setIsTTY(false);
+			writeAuthConfigFile({ api_token: "cached-api-token" });
+			writeWranglerConfig();
+			writeWorkerSource();
+			mockSubDomainRequest();
+			mockUploadWorkerRequest();
+
+			let previewAccountRequests = 0;
+			msw.use(
+				http.post(temporaryPreviewAccountUrl, async () => {
+					previewAccountRequests += 1;
+					return HttpResponse.json({});
+				})
+			);
+
+			await expect(
+				runWrangler("deploy index.js --temporary")
+			).rejects.toThrowError(
+				/You're already authenticated with Cloudflare, so `--temporary` can't be used\./
+			);
+
+			expect(previewAccountRequests).toBe(0);
+			expect(std.out).not.toContain("Temporary account ready:");
+		});
+
+		describe("with temporary preview accounts", () => {
+			it("creates a temporary preview account in non-interactive mode after printing terms notice", async ({
+				expect,
+			}) => {
+				setIsTTY(false);
+				writeWranglerConfig();
+				writeWorkerSource();
+				mockSubDomainRequest("test-sub-domain", true, false);
+				mockUploadWorkerRequest({
+					expectedAccountId: "preview-account-id",
+				});
+
+				let previewRequestBody: unknown;
+				let previewContentType: string | null = null;
+				mockTemporaryPreviewChallenge();
+				msw.use(
+					http.get(
+						"*/accounts/preview-account-id/workers/services/:scriptName",
+						() => {
+							return HttpResponse.json(
+								createFetchResult({
+									default_environment: {
+										script: { last_deployed_from: "wrangler" },
+									},
+								})
+							);
+						}
+					),
+					http.post(temporaryPreviewAccountUrl, async ({ request }) => {
+						previewContentType = request.headers.get("Content-Type");
+						previewRequestBody = await request.json();
+						return HttpResponse.json({
+							success: true,
+							result: {
+								account: {
+									id: "preview-account-id",
+									name: "Preview Account Alpha",
+									type: "standard",
+									apiToken: "preview-account-token",
+									tokenId: "preview-token-id",
+									expiresAt: "2027-01-01T00:00:00.000Z",
+								},
+								claim: {
+									token: "claim-token",
+									url: "https://dash.cloudflare.com/claim-preview?claimToken=claim-token",
+									expiresAt: "2027-01-02T00:00:00.000Z",
+								},
+							},
+							errors: [],
+							messages: [],
+						});
+					})
+				);
+
+				await expect(
+					runWrangler("deploy index.js --temporary")
+				).resolves.toBeUndefined();
+
+				const globalTemporaryAccountPath = path.join(
+					getGlobalWranglerConfigPath(),
+					"wrangler-temporary-account.toml"
+				);
+				const localTemporaryAccountPath = path.join(
+					process.cwd(),
+					".wrangler",
+					"cache",
+					"wrangler-temporary-account.toml"
+				);
+
+				expect(previewContentType).toBe("application/json");
+				expect(previewRequestBody).toEqual({
+					termsOfService: "https://www.cloudflare.com/terms/",
+					privacyPolicy: "https://www.cloudflare.com/privacypolicy/",
+					acceptTermsOfService: "yes",
+					challengeToken: "challenge-token",
+					solution: { checkpoints: expect.any(String) },
+				});
+				const { solution } = previewRequestBody as {
+					solution: { checkpoints: string };
+				};
+				// k+1 checkpoints of 32 bytes each (challenge mock uses k=2).
+				expect(Buffer.from(solution.checkpoints, "base64").length).toBe(
+					(2 + 1) * 32
+				);
+				expect(std.err).toMatchInlineSnapshot(`""`);
+				expect(std.out).not.toContain("Attempting to login via OAuth...");
+				expect(std.out).toContain(TEMPORARY_TERMS_NOTICE);
+				expect(std.out).toContain("Temporary account ready:");
+				expect(std.out).toContain("Account: Preview Account Alpha (created)");
+				expect(std.out).toContain("Claim within:");
+				expect(fs.existsSync(globalTemporaryAccountPath)).toBe(true);
+				expect(fs.existsSync(localTemporaryAccountPath)).toBe(false);
+				if (process.platform !== "win32") {
+					expect(fs.statSync(globalTemporaryAccountPath).mode & 0o777).toBe(
+						0o600
+					);
+				}
+				expect(
+					TOML.parse(fs.readFileSync(globalTemporaryAccountPath, "utf-8"))
+				).toMatchObject({
+					account: {
+						id: "preview-account-id",
+						apiToken: "preview-account-token",
+					},
+					claim: {
+						url: "https://dash.cloudflare.com/claim-preview?claimToken=claim-token",
+					},
+				});
+			});
+
+			it("throws when an OAuth token is on disk, even if it is expired and cannot refresh", async ({
+				expect,
+			}) => {
+				setIsTTY(true);
+				// A stored OAuth token counts as being authenticated even when
+				// expired — it would be refreshed on the next deploy — so
+				// `--temporary` must refuse rather than provision a throwaway
+				// account alongside it.
+				writeAuthConfigFile({
+					oauth_token: "expired-token",
+					refresh_token: "expired-refresh-token",
+					expiration_time: new Date(Date.now() - 1000).toISOString(),
+				});
+				writeWranglerConfig();
+				writeWorkerSource();
+
+				let previewAccountRequests = 0;
+				msw.use(
+					http.post(temporaryPreviewAccountUrl, async () => {
+						previewAccountRequests += 1;
+						return HttpResponse.json({});
+					})
+				);
+
+				await expect(
+					runWrangler("deploy index.js --temporary")
+				).rejects.toThrowError(
+					/You're already authenticated with Cloudflare, so `--temporary` can't be used\./
+				);
+
+				expect(previewAccountRequests).toBe(0);
+				expect(std.out).not.toContain("Temporary account ready:");
+			});
+
+			it("provisions the preview account against the staging API and caches it per-environment", async ({
+				expect,
+			}) => {
+				vi.stubEnv("WRANGLER_API_ENVIRONMENT", "staging");
+				setIsTTY(true);
+				mockPrompt({ text: TEMPORARY_TERMS_PROMPT, result: "yes" });
+				writeWranglerConfig();
+				writeWorkerSource();
+				mockSubDomainRequest("test-sub-domain", true, false);
+				mockUploadWorkerRequest({
+					expectedAccountId: "preview-account-id",
+					expectedBaseUrl: "api.staging.cloudflare.com",
+				});
+
+				let stagingPreviewRequests = 0;
+				mockTemporaryPreviewChallenge(
+					"https://api.staging.cloudflare.com/client/v4/provisioning/previews/challenge"
+				);
+				msw.use(
+					http.get(
+						"*/accounts/preview-account-id/workers/services/:scriptName",
+						() => {
+							return HttpResponse.json(
+								createFetchResult({
+									default_environment: {
+										script: { last_deployed_from: "wrangler" },
+									},
+								})
+							);
+						}
+					),
+					http.post(
+						"https://api.staging.cloudflare.com/client/v4/provisioning/previews",
+						async () => {
+							stagingPreviewRequests++;
+							return HttpResponse.json({
+								success: true,
+								result: {
+									account: {
+										id: "preview-account-id",
+										name: "Preview Account Alpha",
+										type: "standard",
+										apiToken: "preview-account-token",
+										tokenId: "preview-token-id",
+										expiresAt: "2027-01-01T00:00:00.000Z",
+									},
+									claim: {
+										token: "claim-token",
+										url: "https://dash.staging.cloudflare.com/claim-preview?claimToken=claim-token",
+										expiresAt: "2027-01-02T00:00:00.000Z",
+									},
+								},
+								errors: [],
+								messages: [],
+							});
+						}
+					)
+				);
+
+				await expect(
+					runWrangler("deploy index.js --temporary")
+				).resolves.toBeUndefined();
+
+				const stagingTemporaryAccountPath = path.join(
+					getGlobalWranglerConfigPath(),
+					"wrangler-temporary-account.staging.toml"
+				);
+				const productionTemporaryAccountPath = path.join(
+					getGlobalWranglerConfigPath(),
+					"wrangler-temporary-account.toml"
+				);
+
+				expect(stagingPreviewRequests).toBe(1);
+				expect(std.err).toMatchInlineSnapshot(`""`);
+				expect(std.out).toContain("Temporary account ready:");
+				expect(std.out).toContain("Account: Preview Account Alpha (created)");
+				expect(fs.existsSync(stagingTemporaryAccountPath)).toBe(true);
+				expect(fs.existsSync(productionTemporaryAccountPath)).toBe(false);
+			});
+
+			it("reuses a cached temporary preview account for later temporary deploys", async ({
+				expect,
+			}) => {
+				setIsTTY(true);
+				mockPrompt({ text: TEMPORARY_TERMS_PROMPT, result: "yes" });
+				writeWranglerConfig();
+				writeWorkerSource();
+				mockSubDomainRequest("test-sub-domain", true, false);
+				mockUploadWorkerRequest({
+					expectedAccountId: "preview-account-id",
+				});
+
+				let previewAccountRequests = 0;
+				mockTemporaryPreviewChallenge();
+				msw.use(
+					http.get(
+						"*/accounts/preview-account-id/workers/services/:scriptName",
+						() => {
+							return HttpResponse.json(
+								createFetchResult({
+									default_environment: {
+										script: { last_deployed_from: "wrangler" },
+									},
+								})
+							);
+						}
+					),
+					http.get(
+						"*/accounts/preview-account-id/workers/scripts/:scriptName/subdomain",
+						() => {
+							return HttpResponse.json(
+								createFetchResult({ enabled: true, previews_enabled: true })
+							);
+						}
+					),
+					http.post(
+						"*/accounts/preview-account-id/workers/scripts/:scriptName/subdomain",
+						() => {
+							return HttpResponse.json(
+								createFetchResult({ enabled: true, previews_enabled: true })
+							);
+						}
+					),
+					http.get(
+						"*/accounts/preview-account-id/workers/scripts/:scriptName/deployments",
+						() => {
+							return HttpResponse.json(createFetchResult({ deployments: [] }));
+						}
+					),
+					http.post(temporaryPreviewAccountUrl, async () => {
+						previewAccountRequests += 1;
+						return HttpResponse.json({
+							success: true,
+							result: {
+								account: {
+									id: "preview-account-id",
+									name: "Preview Account Alpha",
+									type: "standard",
+									apiToken: "preview-account-token",
+									tokenId: "preview-token-id",
+									expiresAt: "2027-01-01T00:00:00.000Z",
+								},
+								claim: {
+									token: "claim-token",
+									url: "https://dash.cloudflare.com/claim-preview?claimToken=claim-token",
+									expiresAt: "2027-01-02T00:00:00.000Z",
+								},
+							},
+							errors: [],
+							messages: [],
+						});
+					})
+				);
+
+				await expect(
+					runWrangler("deploy index.js --temporary")
+				).resolves.toBeUndefined();
+				await expect(
+					runWrangler("deploy index.js --temporary")
+				).resolves.toBeUndefined();
+
+				expect(previewAccountRequests).toBe(1);
+				expect(std.out).toContain("Temporary account ready:");
+				expect(std.out).toContain("Account: Preview Account Alpha (reused)");
+			});
+
+			it("treats a malformed temporary preview account cache as a miss and refetches", async ({
+				expect,
+			}) => {
+				setIsTTY(true);
+				mockPrompt({ text: TEMPORARY_TERMS_PROMPT, result: "yes" });
+				writeWranglerConfig();
+				writeWorkerSource();
+				mockSubDomainRequest("test-sub-domain", true, false);
+				mockUploadWorkerRequest({
+					expectedAccountId: "preview-account-id",
+				});
+
+				// Plant a cache file that satisfies the top-level shape check but
+				// is missing the nested `account` and `claim` objects. Prior to
+				// the optional-chaining fix this crashed with a TypeError when
+				// reading `.account.expiresAt`.
+				const cachePath = path.join(
+					getGlobalWranglerConfigPath(),
+					"wrangler-temporary-account.toml"
+				);
+				fs.mkdirSync(path.dirname(cachePath), { recursive: true });
+				fs.writeFileSync(
+					cachePath,
+					TOML.stringify({ temporaryPreviewAccount: {} })
+				);
+
+				let previewAccountRequests = 0;
+				mockTemporaryPreviewChallenge();
+				msw.use(
+					http.get(
+						"*/accounts/preview-account-id/workers/services/:scriptName",
+						() => {
+							return HttpResponse.json(
+								createFetchResult({
+									default_environment: {
+										script: { last_deployed_from: "wrangler" },
+									},
+								})
+							);
+						}
+					),
+					http.post(temporaryPreviewAccountUrl, async () => {
+						previewAccountRequests += 1;
+						return HttpResponse.json({
+							success: true,
+							result: {
+								account: {
+									id: "preview-account-id",
+									name: "Preview Account Alpha",
+									type: "standard",
+									apiToken: "preview-account-token",
+									tokenId: "preview-token-id",
+									expiresAt: "2027-01-01T00:00:00.000Z",
+								},
+								claim: {
+									token: "claim-token",
+									url: "https://dash.cloudflare.com/claim-preview?claimToken=claim-token",
+									expiresAt: "2027-01-02T00:00:00.000Z",
+								},
+							},
+							errors: [],
+							messages: [],
+						});
+					})
+				);
+
+				await expect(
+					runWrangler("deploy index.js --temporary")
+				).resolves.toBeUndefined();
+
+				expect(previewAccountRequests).toBe(1);
+				expect(std.out).toContain("Account: Preview Account Alpha (created)");
+				expect(TOML.parse(fs.readFileSync(cachePath, "utf-8"))).toMatchObject({
+					account: { id: "preview-account-id" },
+					claim: {
+						url: "https://dash.cloudflare.com/claim-preview?claimToken=claim-token",
+					},
+				});
+			});
+
 			it("should not throw an error in non-TTY if 'CLOUDFLARE_API_TOKEN' & 'account_id' are in scope", async ({
 				expect,
 			}) => {
@@ -1005,12 +1542,72 @@ describe("deploy", () => {
 
 				await expect(runWrangler("deploy index.js")).rejects.toThrowError();
 
-				expect(std.err).toMatchInlineSnapshot(`
-			          "X [ERROR] In a non-interactive environment, it's necessary to set a CLOUDFLARE_API_TOKEN environment variable for wrangler to work. Please go to https://developers.cloudflare.com/fundamentals/api/get-started/create-token/ for instructions on how to create an api token, and assign its value to CLOUDFLARE_API_TOKEN.
+				expect(std.err).toContain(
+					"In a non-interactive environment, it's necessary to set a CLOUDFLARE_API_TOKEN environment variable"
+				);
+				expect(std.err).toContain(
+					"To continue without logging in, rerun this command with"
+				);
+				expect(std.err).toContain("--temporary");
+			});
 
-			          "
-		        `);
+			it("should fail clearly if the temporary preview account request fails", async ({
+				expect,
+			}) => {
+				setIsTTY(true);
+				mockPrompt({ text: TEMPORARY_TERMS_PROMPT, result: "yes" });
+				writeWranglerConfig();
+				writeWorkerSource();
+
+				mockTemporaryPreviewChallenge();
+				msw.use(
+					http.post(temporaryPreviewAccountUrl, async () => {
+						return new HttpResponse(null, {
+							status: 500,
+							statusText: "Internal Server Error",
+						});
+					})
+				);
+
+				await expect(
+					runWrangler("deploy index.js --temporary")
+				).rejects.toThrowErrorMatchingInlineSnapshot(
+					`[Error: Failed to create a temporary preview account (500 Internal Server Error).]`
+				);
 			});
+
+			it("fails the deploy when the proof-of-work challenge can't be obtained", async ({
+				expect,
+			}) => {
+				setIsTTY(true);
+				mockPrompt({ text: TEMPORARY_TERMS_PROMPT, result: "yes" });
+				writeWranglerConfig();
+				writeWorkerSource();
+
+				let previewRequests = 0;
+				msw.use(
+					http.post(
+						`${temporaryPreviewAccountUrl}/challenge`,
+						() =>
+							new HttpResponse(null, {
+								status: 500,
+								statusText: "Internal Server Error",
+							})
+					),
+					http.post(temporaryPreviewAccountUrl, async () => {
+						previewRequests += 1;
+						return HttpResponse.json({});
+					})
+				);
+
+				await expect(
+					runWrangler("deploy index.js --temporary")
+				).rejects.toThrowErrorMatchingInlineSnapshot(
+					`[Error: Failed to request a proof-of-work challenge (500 Internal Server Error).]`
+				);
+				expect(previewRequests).toBe(0);
+			});
+
 			it("should throw error with no account ID provided and no members retrieved", async ({
 				expect,
 			}) => {
diff --git a/packages/wrangler/src/__tests__/experimental-commands-api.test.ts b/packages/wrangler/src/__tests__/experimental-commands-api.test.ts
index 4a2f2b845a..4b2757da92 100644
--- a/packages/wrangler/src/__tests__/experimental-commands-api.test.ts
+++ b/packages/wrangler/src/__tests__/experimental-commands-api.test.ts
@@ -1,5 +1,6 @@
 import { assert, describe, test } from "vitest";
 import { experimental_getWranglerCommands } from "../experimental-commands-api";
+import type { DefinitionTreeNode } from "../core/types";
 
 describe("experimental_getWranglerCommands", () => {
 	test("returns global flags", ({ expect }) => {
@@ -131,4 +132,101 @@ describe("experimental_getWranglerCommands", () => {
 			"stable",
 		]).toContain(metadata.status);
 	});
+
+	test("commands opting in to `--temporary` match the expected set", ({
+		expect,
+	}) => {
+		const supporting: string[] = [];
+		const walk = (node: DefinitionTreeNode) => {
+			if (
+				node.definition?.type === "command" &&
+				node.definition.behaviour?.supportTemporary
+			) {
+				supporting.push(node.definition.command);
+			}
+			for (const child of node.subtree.values()) {
+				walk(child);
+			}
+		};
+		walk(experimental_getWranglerCommands().registry);
+
+		expect(supporting.sort()).toMatchInlineSnapshot(`
+			[
+			  "wrangler cert delete",
+			  "wrangler cert list",
+			  "wrangler cert upload certificate-authority",
+			  "wrangler cert upload mtls-certificate",
+			  "wrangler d1 create",
+			  "wrangler d1 delete",
+			  "wrangler d1 execute",
+			  "wrangler d1 export",
+			  "wrangler d1 info",
+			  "wrangler d1 insights",
+			  "wrangler d1 list",
+			  "wrangler d1 migrations apply",
+			  "wrangler d1 migrations create",
+			  "wrangler d1 migrations list",
+			  "wrangler d1 time-travel info",
+			  "wrangler d1 time-travel restore",
+			  "wrangler delete",
+			  "wrangler deploy",
+			  "wrangler deployments list",
+			  "wrangler deployments status",
+			  "wrangler deployments view",
+			  "wrangler hyperdrive create",
+			  "wrangler hyperdrive delete",
+			  "wrangler hyperdrive get",
+			  "wrangler hyperdrive list",
+			  "wrangler hyperdrive update",
+			  "wrangler kv bulk delete",
+			  "wrangler kv bulk get",
+			  "wrangler kv bulk put",
+			  "wrangler kv key delete",
+			  "wrangler kv key get",
+			  "wrangler kv key list",
+			  "wrangler kv key put",
+			  "wrangler kv namespace create",
+			  "wrangler kv namespace delete",
+			  "wrangler kv namespace list",
+			  "wrangler kv namespace rename",
+			  "wrangler queues consumer add",
+			  "wrangler queues consumer http add",
+			  "wrangler queues consumer http list",
+			  "wrangler queues consumer http remove",
+			  "wrangler queues consumer list",
+			  "wrangler queues consumer remove",
+			  "wrangler queues consumer worker add",
+			  "wrangler queues consumer worker list",
+			  "wrangler queues consumer worker remove",
+			  "wrangler queues create",
+			  "wrangler queues delete",
+			  "wrangler queues info",
+			  "wrangler queues list",
+			  "wrangler queues pause-delivery",
+			  "wrangler queues purge",
+			  "wrangler queues resume-delivery",
+			  "wrangler queues subscription create",
+			  "wrangler queues subscription delete",
+			  "wrangler queues subscription get",
+			  "wrangler queues subscription list",
+			  "wrangler queues subscription update",
+			  "wrangler queues update",
+			  "wrangler rollback",
+			  "wrangler secret bulk",
+			  "wrangler secret delete",
+			  "wrangler secret list",
+			  "wrangler secret put",
+			  "wrangler tail",
+			  "wrangler triggers deploy",
+			  "wrangler versions deploy",
+			  "wrangler versions list",
+			  "wrangler versions secret bulk",
+			  "wrangler versions secret delete",
+			  "wrangler versions secret list",
+			  "wrangler versions secret put",
+			  "wrangler versions upload",
+			  "wrangler versions view",
+			]
+		`);
+	});
 });
diff --git a/packages/wrangler/src/__tests__/helpers/mock-upload-worker.ts b/packages/wrangler/src/__tests__/helpers/mock-upload-worker.ts
index 1113c1b6f7..060ef95166 100644
--- a/packages/wrangler/src/__tests__/helpers/mock-upload-worker.ts
+++ b/packages/wrangler/src/__tests__/helpers/mock-upload-worker.ts
@@ -31,6 +31,8 @@ export function mockUploadWorkerRequest(
 	options: {
 		wranglerConfigPath?: string;
 		expectedBaseUrl?: string;
+		expectedAccountId?: string;
+		expectedAuthToken?: string;
 		expectedEntry?: string | RegExp | ((entry: string | null) => void);
 		expectedMainModule?: string;
 		expectedType?: "esm" | "sw" | "none";
@@ -68,7 +70,14 @@ export function mockUploadWorkerRequest(
 		expect(url.hostname).toMatch(
 			options.expectedBaseUrl ?? "api.cloudflare.com"
 		);
-		expect(params.accountId).toEqual("some-account-id");
+		expect(params.accountId).toEqual(
+			options.expectedAccountId ?? "some-account-id"
+		);
+		if (options.expectedAuthToken !== undefined) {
+			expect(request.headers.get("Authorization")).toEqual(
+				`Bearer ${options.expectedAuthToken}`
+			);
+		}
 		expect(params.scriptName).toEqual(expectedScriptName);
 		if (useServiceEnvironments) {
 			expect(params.envName).toEqual(env);
@@ -307,6 +316,7 @@ export function mockUploadWorkerRequest(
 		previews_enabled: subdomainDefaults.preview_urls,
 		env,
 		useServiceEnvironments,
+		expectedAccountId: options.expectedAccountId,
 		expectedScriptName,
 	});
 	const subdomainValues = getSubdomainValues(
@@ -323,6 +333,7 @@ export function mockUploadWorkerRequest(
 		},
 		env,
 		useServiceEnvironments,
+		expectedAccountId: options.expectedAccountId,
 		expectedScriptName,
 	});
 }
diff --git a/packages/wrangler/src/__tests__/helpers/mock-workers-subdomain.ts b/packages/wrangler/src/__tests__/helpers/mock-workers-subdomain.ts
index 5647639f51..f3f3e7168e 100644
--- a/packages/wrangler/src/__tests__/helpers/mock-workers-subdomain.ts
+++ b/packages/wrangler/src/__tests__/helpers/mock-workers-subdomain.ts
@@ -41,6 +41,7 @@ export function mockGetWorkerSubdomain({
 	previews_enabled = enabled,
 	env,
 	useServiceEnvironments = true,
+	expectedAccountId = "some-account-id",
 	expectedScriptName = "test-name" +
 		(!useServiceEnvironments && env ? `-${env}` : ""),
 }: {
@@ -48,6 +49,7 @@ export function mockGetWorkerSubdomain({
 	previews_enabled?: boolean;
 	env?: string | undefined;
 	useServiceEnvironments?: boolean | undefined;
+	expectedAccountId?: string;
 	expectedScriptName?: string | false;
 }) {
 	const url =
@@ -58,7 +60,7 @@ export function mockGetWorkerSubdomain({
 		http.get(
 			url,
 			({ params }) => {
-				assert(params.accountId === "some-account-id");
+				assert(params.accountId === expectedAccountId);
 				if (expectedScriptName !== false) {
 					assert(params.scriptName === expectedScriptName);
 				}
@@ -85,6 +87,7 @@ export function mockUpdateWorkerSubdomain({
 	},
 	env,
 	useServiceEnvironments = true,
+	expectedAccountId = "some-account-id",
 	expectedScriptName = "test-name" +
 		(!useServiceEnvironments && env ? `-${env}` : ""),
 	flakeCount = 0,
@@ -99,6 +102,7 @@ export function mockUpdateWorkerSubdomain({
 	};
 	env?: string | undefined;
 	useServiceEnvironments?: boolean | undefined;
+	expectedAccountId?: string;
 	expectedScriptName?: string | false;
 	flakeCount?: number; // The first `flakeCount` requests will fail with a 500 error
 }) {
@@ -111,7 +115,7 @@ export function mockUpdateWorkerSubdomain({
 		http.post(
 			url,
 			async ({ request, params }) => {
-				assert(params.accountId === "some-account-id");
+				assert(params.accountId === expectedAccountId);
 				if (expectedScriptName !== false) {
 					assert(params.scriptName === expectedScriptName);
 				}
diff --git a/packages/wrangler/src/__tests__/index.test.ts b/packages/wrangler/src/__tests__/index.test.ts
index abd852bfa0..e554d60a1d 100644
--- a/packages/wrangler/src/__tests__/index.test.ts
+++ b/packages/wrangler/src/__tests__/index.test.ts
@@ -2,12 +2,13 @@ import {
 	runInTempDir,
 	writeWranglerConfig,
 } from "@cloudflare/workers-utils/test-helpers";
-import { beforeEach, describe, it, vi } from "vitest";
+import { afterEach, beforeEach, describe, it, vi } from "vitest";
 import { getPackageManager } from "../package-manager";
 import { updateCheck } from "../update-check";
 import { logPossibleBugMessage } from "../utils/logPossibleBugMessage";
 import { endEventLoop } from "./helpers/end-event-loop";
 import { mockConsoleMethods } from "./helpers/mock-console";
+import { clearDialogs } from "./helpers/mock-dialogs";
 import { runWrangler } from "./helpers/run-wrangler";
 import { writeWorkerSource } from "./helpers/write-worker-source";
 import type { PackageManager } from "../package-manager";
@@ -28,6 +29,10 @@ describe("wrangler", () => {
 		(getPackageManager as Mock).mockResolvedValue(mockPackageManager);
 	});
 
+	afterEach(() => {
+		clearDialogs();
+	});
+
 	const std = mockConsoleMethods();
 
 	describe("no command", () => {
@@ -104,6 +109,24 @@ describe("wrangler", () => {
 
 			expect(std.err).toMatchInlineSnapshot(`""`);
 		});
+
+		it("should not require temporary terms acceptance before root help", async ({
+			expect,
+		}) => {
+			await runWrangler("--help --temporary");
+
+			expect(std.out).toContain("wrangler");
+			expect(std.out).toContain("COMMANDS");
+			expect(std.err).toMatchInlineSnapshot(`""`);
+		});
+	});
+
+	describe("--temporary", () => {
+		it("is rejected on commands that don't opt in", async ({ expect }) => {
+			await expect(runWrangler("whoami --temporary")).rejects.toThrowError(
+				/Unknown argument: temporary/
+			);
+		});
 	});
 
 	describe("invalid command", () => {
diff --git a/packages/wrangler/src/__tests__/logout.test.ts b/packages/wrangler/src/__tests__/logout.test.ts
index abf6703c0c..de42c41549 100644
--- a/packages/wrangler/src/__tests__/logout.test.ts
+++ b/packages/wrangler/src/__tests__/logout.test.ts
@@ -1,4 +1,6 @@
 import fs from "node:fs";
+import path from "node:path";
+import { getGlobalWranglerConfigPath } from "@cloudflare/workers-utils";
 import {
 	runInTempDir,
 	writeWranglerConfig,
@@ -26,6 +28,30 @@ describe("logout", () => {
 		`);
 	});
 
+	it("should clear a cached temporary preview account when not logged in via OAuth", async ({
+		expect,
+	}) => {
+		const temporaryAccountConfigPath = path.join(
+			getGlobalWranglerConfigPath(),
+			"wrangler-temporary-account.toml"
+		);
+		fs.mkdirSync(path.dirname(temporaryAccountConfigPath), { recursive: true });
+		fs.writeFileSync(
+			temporaryAccountConfigPath,
+			JSON.stringify({ temporaryPreviewAccount: { account: {}, claim: {} } })
+		);
+
+		await runWrangler("logout", { CLOUDFLARE_API_TOKEN: undefined });
+
+		expect(std.out).toMatchInlineSnapshot(`
+			"
+			 ⛅️ wrangler x.x.x
+			──────────────────
+			Cleared temporary preview account."
+		`);
+		expect(fs.existsSync(temporaryAccountConfigPath)).toBeFalsy();
+	});
+
 	it("should exit with a message stating the user logged in via API token", async ({
 		expect,
 	}) => {
@@ -43,10 +69,19 @@ describe("logout", () => {
 	it("should logout user that has been properly logged in", async ({
 		expect,
 	}) => {
+		const temporaryAccountConfigPath = path.join(
+			getGlobalWranglerConfigPath(),
+			"wrangler-temporary-account.toml"
+		);
 		writeAuthConfigFile({
 			oauth_token: "some-oauth-tok",
 			refresh_token: "some-refresh-tok",
 		});
+		fs.mkdirSync(path.dirname(temporaryAccountConfigPath), { recursive: true });
+		fs.writeFileSync(
+			temporaryAccountConfigPath,
+			JSON.stringify({ temporaryPreviewAccount: { account: {}, claim: {} } })
+		);
 		// Make sure that logout removed the config file containing the auth tokens.
 		const config = getAuthConfigFilePath();
 		let counter = 0;
@@ -63,6 +98,7 @@ describe("logout", () => {
 		);
 
 		expect(fs.existsSync(config)).toBeTruthy();
+		expect(fs.existsSync(temporaryAccountConfigPath)).toBeTruthy();
 
 		await runWrangler("logout", { CLOUDFLARE_API_TOKEN: undefined });
 
@@ -73,6 +109,7 @@ describe("logout", () => {
 			Successfully logged out."
 		`);
 		expect(fs.existsSync(config)).toBeFalsy();
+		expect(fs.existsSync(temporaryAccountConfigPath)).toBeFalsy();
 		expect(counter).toBe(1);
 	});
 
diff --git a/packages/wrangler/src/__tests__/user.test.ts b/packages/wrangler/src/__tests__/user.test.ts
index 0b656b6735..1ef9b1839e 100644
--- a/packages/wrangler/src/__tests__/user.test.ts
+++ b/packages/wrangler/src/__tests__/user.test.ts
@@ -1,3 +1,5 @@
+import fs from "node:fs";
+import path from "node:path";
 import {
 	COMPLIANCE_REGION_CONFIG_UNKNOWN,
 	getGlobalWranglerConfigPath,
@@ -97,6 +99,48 @@ describe("User", () => {
 			});
 		});
 
+		it("should clear the cached temporary preview account when logging in", async ({
+			expect,
+		}) => {
+			// Resolve the path inside the test so it picks up the HOME/XDG_CONFIG_HOME
+			// stubs set by runInTempDir's beforeEach, rather than the real homedir.
+			const temporaryAccountConfigPath = path.join(
+				getGlobalWranglerConfigPath(),
+				"wrangler-temporary-account.toml"
+			);
+
+			mockOAuthServerCallback("success");
+
+			fs.mkdirSync(path.dirname(temporaryAccountConfigPath), {
+				recursive: true,
+			});
+			fs.writeFileSync(
+				temporaryAccountConfigPath,
+				JSON.stringify({ temporaryPreviewAccount: { account: {}, claim: {} } })
+			);
+
+			msw.use(
+				http.post(
+					"*/oauth2/token",
+					async () => {
+						return HttpResponse.json({
+							access_token: "test-access-token",
+							expires_in: 100000,
+							refresh_token: "test-refresh-token",
+							scope: "account:read",
+						});
+					},
+					{ once: true }
+				)
+			);
+
+			expect(fs.existsSync(temporaryAccountConfigPath)).toBe(true);
+
+			await runWrangler("login");
+
+			expect(fs.existsSync(temporaryAccountConfigPath)).toBe(false);
+		});
+
 		it("should login a user when `wrangler login` is run with an ip address for custom callback-host", async ({
 			expect,
 		}) => {
diff --git a/packages/wrangler/src/__tests__/versions/versions.upload.test.ts b/packages/wrangler/src/__tests__/versions/versions.upload.test.ts
index 64123d6263..29d7f264b9 100644
--- a/packages/wrangler/src/__tests__/versions/versions.upload.test.ts
+++ b/packages/wrangler/src/__tests__/versions/versions.upload.test.ts
@@ -1,6 +1,7 @@
 import assert from "node:assert";
 import * as fs from "node:fs";
 import { generatePreviewAlias } from "@cloudflare/deploy-helpers";
+import { TEMPORARY_TERMS_NOTICE } from "@cloudflare/workers-auth";
 import {
 	runInTempDir,
 	writeRedirectedWranglerConfig,
@@ -36,6 +37,8 @@ describe("versions upload", () => {
 	const { setIsTTY } = useMockIsTTY();
 	const std = mockConsoleMethods();
 	const assertApiRequest = makeApiRequestAsserter(std);
+	const temporaryPreviewAccountUrl =
+		"https://api.cloudflare.com/client/v4/provisioning/previews";
 
 	function mockGetScript(result?: unknown) {
 		msw.use(
@@ -133,6 +136,76 @@ describe("versions upload", () => {
 		) as WorkerMetadata;
 	}
 
+	describe("with --temporary", () => {
+		mockAccountId({ accountId: null });
+		mockApiToken({ apiToken: null });
+
+		test("should create a temporary account in non-interactive mode after printing terms notice", async ({
+			expect,
+		}) => {
+			let previewAccountRequests = 0;
+			msw.use(
+				http.post(`${temporaryPreviewAccountUrl}/challenge`, () =>
+					HttpResponse.json({
+						success: true,
+						result: {
+							challengeToken: "challenge-token",
+							seed: Buffer.alloc(32, 1).toString("base64url"),
+							k: 2,
+							g: 2,
+							s: 16,
+							expiresAt: 9999999999,
+						},
+						errors: [],
+						messages: [],
+					})
+				),
+				http.post(temporaryPreviewAccountUrl, async () => {
+					previewAccountRequests += 1;
+					return HttpResponse.json({
+						success: true,
+						result: {
+							account: {
+								id: "preview-account-id",
+								name: "Preview Account Alpha",
+								type: "standard",
+								apiToken: "preview-account-token",
+								tokenId: "preview-token-id",
+								expiresAt: "2027-01-01T00:00:00.000Z",
+							},
+							claim: {
+								token: "claim-token",
+								url: "https://dash.cloudflare.com/claim-preview?claimToken=claim-token",
+								expiresAt: "2027-01-02T00:00:00.000Z",
+							},
+						},
+						errors: [],
+						messages: [],
+					});
+				})
+			);
+
+			mockGetScript();
+			mockUploadVersion(false, 0);
+			writeWranglerConfig({
+				name: "test-name",
+				main: "./index.js",
+			});
+			writeWorkerSource();
+			setIsTTY(false);
+
+			await expect(
+				runWrangler("versions upload --temporary")
+			).resolves.toBeUndefined();
+
+			expect(previewAccountRequests).toBe(1);
+			expect(std.out).toContain(TEMPORARY_TERMS_NOTICE);
+			expect(std.out).toContain("Temporary account ready:");
+			expect(std.out).toContain("Account: Preview Account Alpha (created)");
+			expect(std.out).toContain("Uploaded test-name");
+		});
+	});
+
 	test("should print bindings & startup time on versions upload", async () => {
 		mockGetScript();
 		mockUploadVersion(false);
diff --git a/packages/wrangler/src/cert/cert.ts b/packages/wrangler/src/cert/cert.ts
index 4d6f3ca617..e8ada94e15 100644
--- a/packages/wrangler/src/cert/cert.ts
+++ b/packages/wrangler/src/cert/cert.ts
@@ -38,6 +38,7 @@ export const certUploadMtlsCommand = createCommand({
 		status: "stable",
 		owner: "Product: SSL",
 	},
+	behaviour: { supportTemporary: true },
 	args: {
 		cert: {
 			description:
@@ -87,6 +88,7 @@ export const certUploadCaCertCommand = createCommand({
 		status: "stable",
 		owner: "Product: SSL",
 	},
+	behaviour: { supportTemporary: true },
 	args: {
 		name: {
 			describe: "The name for the certificate",
@@ -130,6 +132,7 @@ export const certListCommand = createCommand({
 		status: "stable",
 		owner: "Product: SSL",
 	},
+	behaviour: { supportTemporary: true },
 	async handler(_, { config }) {
 		const accountId = await requireAuth(config);
 		const certificates = await listMTlsCertificates(
@@ -165,6 +168,7 @@ export const certDeleteCommand = createCommand({
 		status: "stable",
 		owner: "Product: SSL",
 	},
+	behaviour: { supportTemporary: true },
 	args: {
 		id: {
 			description: "The id of the mTLS certificate to delete",
diff --git a/packages/wrangler/src/core/register-yargs-command.ts b/packages/wrangler/src/core/register-yargs-command.ts
index 62e08e7bef..dac9b8ef6c 100644
--- a/packages/wrangler/src/core/register-yargs-command.ts
+++ b/packages/wrangler/src/core/register-yargs-command.ts
@@ -33,12 +33,14 @@ import {
 } from "../metrics/sanitization";
 import { writeOutput } from "../output";
 import { addBreadcrumb } from "../sentry";
+import { setTemporaryAllowed } from "../user";
 import { dedent } from "../utils/dedent";
 import { isLocal, printResourceLocation } from "../utils/is-local";
 import { printWranglerBanner } from "../wrangler-banner";
 import { CommandHandledError } from "./CommandHandledError";
 import { getErrorType, handleError } from "./handle-errors";
 import { demandSingleValue } from "./helpers";
+import { temporaryArgDefinition } from "./temporary-commands";
 import type { CommonYargsArgv, SubHelp } from "../yargs-types";
 import type {
 	HandlerArgs,
@@ -66,7 +68,9 @@ export function createRegisterYargsCommand(
 			(def.metadata?.hidden ? false : def.metadata?.description) as string, // Cast to satisfy TypeScript overload selection
 			(subYargs) => {
 				if (def.type === "command") {
-					const args = def.args ?? {};
+					const args: NamedArgDefinitions = def.behaviour?.supportTemporary
+						? { ...def.args, temporary: temporaryArgDefinition }
+						: (def.args ?? {});
 
 					const positionalArgs = new Set(def.positionalArgs);
 
@@ -209,6 +213,11 @@ function createHandler(def: InternalCommandDefinition, argv: string[]) {
 						AUTOCREATE_RESOURCES: args.experimentalAutoCreate,
 					};
 
+			setTemporaryAllowed(
+				def.behaviour?.supportTemporary === true &&
+					Boolean((args as { temporary?: boolean }).temporary)
+			);
+
 			await run(experimentalFlags, async () => {
 				const config =
 					(def.behaviour?.provideConfig ?? true)
@@ -368,6 +377,18 @@ function createHandler(def: InternalCommandDefinition, argv: string[]) {
 						def.behaviour
 					);
 
+					// For commands that support `--temporary`, nudge users towards a
+					// temporary account when they hit the non-interactive auth error.
+					if (
+						def.behaviour?.supportTemporary &&
+						err instanceof UserError &&
+						err.telemetryMessage ===
+							"user auth missing api token non interactive"
+					) {
+						err.message +=
+							"\n\nTo continue without logging in, rerun this command with `--temporary`. Wrangler will use a temporary account and print a claim URL.";
+					}
+
 					await handleError(err, args, argv);
 
 					// Wrap the error to signal that the telemetry has already been sent and the error reporting handled.
diff --git a/packages/wrangler/src/core/temporary-commands.ts b/packages/wrangler/src/core/temporary-commands.ts
new file mode 100644
index 0000000000..7edd5f2e47
--- /dev/null
+++ b/packages/wrangler/src/core/temporary-commands.ts
@@ -0,0 +1,7 @@
+export const temporaryArgDefinition = {
+	describe:
+		"Create and use a temporary preview account when no Cloudflare credentials are available",
+	type: "boolean",
+	default: false,
+	hidden: true,
+} as const;
diff --git a/packages/wrangler/src/core/types.ts b/packages/wrangler/src/core/types.ts
index 7893c2e23c..15473cb0e0 100644
--- a/packages/wrangler/src/core/types.ts
+++ b/packages/wrangler/src/core/types.ts
@@ -238,6 +238,15 @@ export type CommandDefinition<
 		suggestSkillsAfterHandler?:
 			| boolean
 			| ((args: HandlerArgs<NamedArgDefs>) => boolean);
+
+		/**
+		 * Whether this command can authenticate with a temporary preview account
+		 * (via the hidden `--temporary` flag) when no real credentials are available.
+		 * Only enable this for commands whose API calls are covered by the temporary
+		 * preview-account deploy token (Workers, KV, D1, Hyperdrive, Queues, SSL/Certs).
+		 * @default false
+		 */
+		supportTemporary?: boolean;
 	};
 
 	/**
diff --git a/packages/wrangler/src/d1/create.ts b/packages/wrangler/src/d1/create.ts
index bfec816aba..23aaea9bd5 100644
--- a/packages/wrangler/src/d1/create.ts
+++ b/packages/wrangler/src/d1/create.ts
@@ -77,6 +77,7 @@ export const d1CreateCommand = createCommand({
 		status: "stable",
 		owner: "Product: D1",
 	},
+	behaviour: { supportTemporary: true },
 	args: {
 		name: {
 			type: "string",
diff --git a/packages/wrangler/src/d1/delete.ts b/packages/wrangler/src/d1/delete.ts
index 78bdc05690..18a38afc1d 100644
--- a/packages/wrangler/src/d1/delete.ts
+++ b/packages/wrangler/src/d1/delete.ts
@@ -16,6 +16,7 @@ export const d1DeleteCommand = createCommand({
 		owner: "Product: D1",
 	},
 	behaviour: {
+		supportTemporary: true,
 		printBanner: true,
 	},
 	args: {
diff --git a/packages/wrangler/src/d1/execute.ts b/packages/wrangler/src/d1/execute.ts
index 386e65104c..a662ce5468 100644
--- a/packages/wrangler/src/d1/execute.ts
+++ b/packages/wrangler/src/d1/execute.ts
@@ -50,6 +50,7 @@ export const d1ExecuteCommand = createCommand({
 			"You must provide either --command or --file for this command to run successfully.",
 	},
 	behaviour: {
+		supportTemporary: true,
 		printBanner: (args) => !args.json,
 		printResourceLocation: (args) => !args.json,
 	},
diff --git a/packages/wrangler/src/d1/export.ts b/packages/wrangler/src/d1/export.ts
index 1f07a129eb..9bd971d805 100644
--- a/packages/wrangler/src/d1/export.ts
+++ b/packages/wrangler/src/d1/export.ts
@@ -28,6 +28,7 @@ export const d1ExportCommand = createCommand({
 		owner: "Product: D1",
 	},
 	behaviour: {
+		supportTemporary: true,
 		printResourceLocation: true,
 	},
 	args: {
diff --git a/packages/wrangler/src/d1/info.ts b/packages/wrangler/src/d1/info.ts
index afc8f5f1ec..437b233dd5 100644
--- a/packages/wrangler/src/d1/info.ts
+++ b/packages/wrangler/src/d1/info.ts
@@ -18,6 +18,7 @@ export const d1InfoCommand = createCommand({
 		owner: "Product: D1",
 	},
 	behaviour: {
+		supportTemporary: true,
 		printBanner: (args) => !args.json,
 	},
 	args: {
diff --git a/packages/wrangler/src/d1/insights.ts b/packages/wrangler/src/d1/insights.ts
index d6f3a6d763..b3b23af86f 100644
--- a/packages/wrangler/src/d1/insights.ts
+++ b/packages/wrangler/src/d1/insights.ts
@@ -71,6 +71,7 @@ export const d1InsightsCommand = createCommand({
 		owner: "Product: D1",
 	},
 	behaviour: {
+		supportTemporary: true,
 		printBanner: (args) => !args.json,
 	},
 	args: {
diff --git a/packages/wrangler/src/d1/list.ts b/packages/wrangler/src/d1/list.ts
index ffc8e1601a..56cbadbb56 100644
--- a/packages/wrangler/src/d1/list.ts
+++ b/packages/wrangler/src/d1/list.ts
@@ -13,6 +13,7 @@ export const d1ListCommand = createCommand({
 		owner: "Product: D1",
 	},
 	behaviour: {
+		supportTemporary: true,
 		printBanner: (args) => !args.json,
 	},
 	args: {
diff --git a/packages/wrangler/src/d1/migrations/apply.ts b/packages/wrangler/src/d1/migrations/apply.ts
index 9a3902886a..a654d08d8f 100644
--- a/packages/wrangler/src/d1/migrations/apply.ts
+++ b/packages/wrangler/src/d1/migrations/apply.ts
@@ -36,6 +36,7 @@ export const d1MigrationsApplyCommand = createCommand({
 		owner: "Product: D1",
 	},
 	behaviour: {
+		supportTemporary: true,
 		printResourceLocation: true,
 	},
 	args: {
diff --git a/packages/wrangler/src/d1/migrations/create.ts b/packages/wrangler/src/d1/migrations/create.ts
index 462e9e92db..7560902a3c 100644
--- a/packages/wrangler/src/d1/migrations/create.ts
+++ b/packages/wrangler/src/d1/migrations/create.ts
@@ -28,6 +28,7 @@ export const d1MigrationsCreateCommand = createCommand({
 		owner: "Product: D1",
 	},
 	behaviour: {
+		supportTemporary: true,
 		printBanner: true,
 	},
 	args: {
diff --git a/packages/wrangler/src/d1/migrations/list.ts b/packages/wrangler/src/d1/migrations/list.ts
index e1350ed8bf..13414eb7d5 100644
--- a/packages/wrangler/src/d1/migrations/list.ts
+++ b/packages/wrangler/src/d1/migrations/list.ts
@@ -18,6 +18,7 @@ export const d1MigrationsListCommand = createCommand({
 		owner: "Product: D1",
 	},
 	behaviour: {
+		supportTemporary: true,
 		printResourceLocation: true,
 	},
 	args: {
diff --git a/packages/wrangler/src/d1/timeTravel/info.ts b/packages/wrangler/src/d1/timeTravel/info.ts
index 502fbc4762..a676680350 100644
--- a/packages/wrangler/src/d1/timeTravel/info.ts
+++ b/packages/wrangler/src/d1/timeTravel/info.ts
@@ -18,6 +18,7 @@ export const d1TimeTravelInfoCommand = createCommand({
 		owner: "Product: D1",
 	},
 	behaviour: {
+		supportTemporary: true,
 		printBanner: (args) => !args.json,
 	},
 	args: {
diff --git a/packages/wrangler/src/d1/timeTravel/restore.ts b/packages/wrangler/src/d1/timeTravel/restore.ts
index 79fe44c70e..a4e30e8547 100644
--- a/packages/wrangler/src/d1/timeTravel/restore.ts
+++ b/packages/wrangler/src/d1/timeTravel/restore.ts
@@ -22,6 +22,7 @@ export const d1TimeTravelRestoreCommand = createCommand({
 		owner: "Product: D1",
 	},
 	behaviour: {
+		supportTemporary: true,
 		printBanner: (args) => !args.json,
 	},
 	args: {
diff --git a/packages/wrangler/src/delete.ts b/packages/wrangler/src/delete.ts
index 38f66ef86f..addc9004a3 100644
--- a/packages/wrangler/src/delete.ts
+++ b/packages/wrangler/src/delete.ts
@@ -66,6 +66,7 @@ export const deleteCommand = createCommand({
 		category: "Compute & AI",
 	},
 	behaviour: {
+		supportTemporary: true,
 		suggestSkillsAfterHandler: true,
 	},
 	args: {
diff --git a/packages/wrangler/src/deploy/index.ts b/packages/wrangler/src/deploy/index.ts
index 4c80437830..c707ef22cc 100644
--- a/packages/wrangler/src/deploy/index.ts
+++ b/packages/wrangler/src/deploy/index.ts
@@ -99,6 +99,7 @@ export const deployCommand = createCommand({
 		},
 	},
 	behaviour: {
+		supportTemporary: true,
 		useConfigRedirectIfAvailable: true,
 		overrideExperimentalFlags: (args) => ({
 			MULTIWORKER: false,
diff --git a/packages/wrangler/src/hyperdrive/create.ts b/packages/wrangler/src/hyperdrive/create.ts
index cb9b17dd91..b5dee5849b 100644
--- a/packages/wrangler/src/hyperdrive/create.ts
+++ b/packages/wrangler/src/hyperdrive/create.ts
@@ -18,6 +18,7 @@ export const hyperdriveCreateCommand = createCommand({
 		status: "stable",
 		owner: "Product: Hyperdrive",
 	},
+	behaviour: { supportTemporary: true },
 	args: {
 		name: {
 			type: "string",
diff --git a/packages/wrangler/src/hyperdrive/delete.ts b/packages/wrangler/src/hyperdrive/delete.ts
index 8b7d0663a3..4a75afc637 100644
--- a/packages/wrangler/src/hyperdrive/delete.ts
+++ b/packages/wrangler/src/hyperdrive/delete.ts
@@ -8,6 +8,7 @@ export const hyperdriveDeleteCommand = createCommand({
 		status: "stable",
 		owner: "Product: Hyperdrive",
 	},
+	behaviour: { supportTemporary: true },
 	args: {
 		id: {
 			type: "string",
diff --git a/packages/wrangler/src/hyperdrive/get.ts b/packages/wrangler/src/hyperdrive/get.ts
index e9871d9ef6..95ae42f2cb 100644
--- a/packages/wrangler/src/hyperdrive/get.ts
+++ b/packages/wrangler/src/hyperdrive/get.ts
@@ -8,6 +8,7 @@ export const hyperdriveGetCommand = createCommand({
 		status: "stable",
 		owner: "Product: Hyperdrive",
 	},
+	behaviour: { supportTemporary: true },
 	args: {
 		id: {
 			type: "string",
diff --git a/packages/wrangler/src/hyperdrive/list.ts b/packages/wrangler/src/hyperdrive/list.ts
index 4f260a297d..1b1b75325f 100644
--- a/packages/wrangler/src/hyperdrive/list.ts
+++ b/packages/wrangler/src/hyperdrive/list.ts
@@ -9,6 +9,7 @@ export const hyperdriveListCommand = createCommand({
 		status: "stable",
 		owner: "Product: Hyperdrive",
 	},
+	behaviour: { supportTemporary: true },
 	args: {},
 	async handler(_, { config }) {
 		logger.log(`📋 Listing Hyperdrive configs`);
diff --git a/packages/wrangler/src/hyperdrive/update.ts b/packages/wrangler/src/hyperdrive/update.ts
index 816aa91c64..f8dbd9d72a 100644
--- a/packages/wrangler/src/hyperdrive/update.ts
+++ b/packages/wrangler/src/hyperdrive/update.ts
@@ -15,6 +15,7 @@ export const hyperdriveUpdateCommand = createCommand({
 		status: "stable",
 		owner: "Product: Hyperdrive",
 	},
+	behaviour: { supportTemporary: true },
 	args: {
 		id: {
 			type: "string",
diff --git a/packages/wrangler/src/kv/index.ts b/packages/wrangler/src/kv/index.ts
index 04be00b65f..7a43496b68 100644
--- a/packages/wrangler/src/kv/index.ts
+++ b/packages/wrangler/src/kv/index.ts
@@ -84,6 +84,7 @@ export const kvNamespaceCreateCommand = createCommand({
 		status: "stable",
 		owner: "Product: KV",
 	},
+	behaviour: { supportTemporary: true },
 
 	args: {
 		namespace: {
@@ -168,7 +169,11 @@ export const kvNamespaceListCommand = createCommand({
 
 	args: {},
 
-	behaviour: { printBanner: false, printResourceLocation: false },
+	behaviour: {
+		supportTemporary: true,
+		printBanner: false,
+		printResourceLocation: false,
+	},
 	async handler(_, { config, sdk }) {
 		const accountId = await requireAuth(config);
 
@@ -196,6 +201,7 @@ export const kvNamespaceDeleteCommand = createCommand({
 		status: "stable",
 		owner: "Product: KV",
 	},
+	behaviour: { supportTemporary: true },
 	positionalArgs: ["namespace"],
 	args: {
 		namespace: {
@@ -315,6 +321,7 @@ export const kvNamespaceRenameCommand = createCommand({
 		status: "stable",
 		owner: "Product: KV",
 	},
+	behaviour: { supportTemporary: true },
 	positionalArgs: ["old-name"],
 	args: {
 		"old-name": {
@@ -471,6 +478,7 @@ export const kvKeyPutCommand = createCommand({
 		owner: "Product: KV",
 	},
 	behaviour: {
+		supportTemporary: true,
 		printResourceLocation: true,
 	},
 	positionalArgs: ["key", "value"],
@@ -564,6 +572,7 @@ export const kvKeyListCommand = createCommand({
 		owner: "Product: KV",
 	},
 	behaviour: {
+		supportTemporary: true,
 		// implicitly expects to output JSON only
 		printResourceLocation: false,
 		printBanner: false,
@@ -688,6 +697,7 @@ export const kvKeyGetCommand = createCommand({
 		owner: "Product: KV",
 	},
 	behaviour: {
+		supportTemporary: true,
 		printBanner: false,
 		printResourceLocation: false,
 	},
@@ -795,6 +805,7 @@ export const kvKeyDeleteCommand = createCommand({
 		owner: "Product: KV",
 	},
 	behaviour: {
+		supportTemporary: true,
 		printResourceLocation: true,
 	},
 	positionalArgs: ["key"],
@@ -847,6 +858,7 @@ export const kvBulkGetCommand = createCommand({
 		owner: "Product: KV",
 	},
 	behaviour: {
+		supportTemporary: true,
 		printBanner: false,
 		printResourceLocation: false,
 	},
@@ -944,6 +956,7 @@ export const kvBulkPutCommand = createCommand({
 		owner: "Product: KV",
 	},
 	behaviour: {
+		supportTemporary: true,
 		printResourceLocation: true,
 	},
 	positionalArgs: ["filename"],
@@ -1069,6 +1082,7 @@ export const kvBulkDeleteCommand = createCommand({
 		owner: "Product: KV",
 	},
 	behaviour: {
+		supportTemporary: true,
 		printResourceLocation: true,
 	},
 	positionalArgs: ["filename"],
diff --git a/packages/wrangler/src/pages/deploy.ts b/packages/wrangler/src/pages/deploy.ts
index 11a7591cc0..3bee673d00 100644
--- a/packages/wrangler/src/pages/deploy.ts
+++ b/packages/wrangler/src/pages/deploy.ts
@@ -188,8 +188,11 @@ export const pagesDeployCommand = createCommand({
 		const configCache = getConfigCache<PagesConfigCache>(
 			PAGES_CONFIG_CACHE_FILENAME
 		);
-		const accountId =
-			getCloudflareAccountIdFromEnv() ?? (await requireAuth(configCache));
+		const envAccountId = getCloudflareAccountIdFromEnv();
+		const accountId = await requireAuth({
+			...configCache,
+			...(envAccountId ? { account_id: envAccountId } : {}),
+		});
 
 		let projectName =
 			args.projectName ?? config?.name ?? configCache.project_name;
diff --git a/packages/wrangler/src/pages/deployment-tails.ts b/packages/wrangler/src/pages/deployment-tails.ts
index 2b9eb240a3..729043b5ca 100644
--- a/packages/wrangler/src/pages/deployment-tails.ts
+++ b/packages/wrangler/src/pages/deployment-tails.ts
@@ -144,8 +144,11 @@ export const pagesDeploymentTailCommand = createCommand({
 		const pagesConfig = getConfigCache<PagesConfigCache>(
 			PAGES_CONFIG_CACHE_FILENAME
 		);
-		const accountId =
-			getCloudflareAccountIdFromEnv() ?? (await requireAuth(pagesConfig));
+		const envAccountId = getCloudflareAccountIdFromEnv();
+		const accountId = await requireAuth({
+			...pagesConfig,
+			...(envAccountId ? { account_id: envAccountId } : {}),
+		});
 		let deploymentId = deployment;
 
 		if (!isInteractive()) {
diff --git a/packages/wrangler/src/pages/deployments.ts b/packages/wrangler/src/pages/deployments.ts
index 6f8b47d801..1f8b04fb35 100644
--- a/packages/wrangler/src/pages/deployments.ts
+++ b/packages/wrangler/src/pages/deployments.ts
@@ -49,8 +49,11 @@ export const pagesDeploymentListCommand = createCommand({
 		const config = getConfigCache<PagesConfigCache>(
 			PAGES_CONFIG_CACHE_FILENAME
 		);
-		const accountId =
-			getCloudflareAccountIdFromEnv() ?? (await requireAuth(config));
+		const envAccountId = getCloudflareAccountIdFromEnv();
+		const accountId = await requireAuth({
+			...config,
+			...(envAccountId ? { account_id: envAccountId } : {}),
+		});
 
 		projectName ??= config.project_name;
 
@@ -149,8 +152,11 @@ export const pagesDeploymentDeleteCommand = createCommand({
 		const config = getConfigCache<PagesConfigCache>(
 			PAGES_CONFIG_CACHE_FILENAME
 		);
-		const accountId =
-			getCloudflareAccountIdFromEnv() ?? (await requireAuth(config));
+		const envAccountId = getCloudflareAccountIdFromEnv();
+		const accountId = await requireAuth({
+			...config,
+			...(envAccountId ? { account_id: envAccountId } : {}),
+		});
 
 		projectName ??= config.project_name;
 
diff --git a/packages/wrangler/src/pages/download-config.ts b/packages/wrangler/src/pages/download-config.ts
index 4b13c2d9f9..f4b18305b3 100644
--- a/packages/wrangler/src/pages/download-config.ts
+++ b/packages/wrangler/src/pages/download-config.ts
@@ -320,8 +320,11 @@ export const pagesDownloadConfigCommand = createCommand({
 		const projectConfig = getConfigCache<PagesConfigCache>(
 			PAGES_CONFIG_CACHE_FILENAME
 		);
-		const accountId =
-			getCloudflareAccountIdFromEnv() ?? (await requireAuth(projectConfig));
+		const envAccountId = getCloudflareAccountIdFromEnv();
+		const accountId = await requireAuth({
+			...projectConfig,
+			...(envAccountId ? { account_id: envAccountId } : {}),
+		});
 
 		projectName ??= projectConfig.project_name;
 
diff --git a/packages/wrangler/src/pages/secret/index.ts b/packages/wrangler/src/pages/secret/index.ts
index 5398a9b48f..def7819d1f 100644
--- a/packages/wrangler/src/pages/secret/index.ts
+++ b/packages/wrangler/src/pages/secret/index.ts
@@ -81,8 +81,11 @@ async function pagesProject(
 	const configCache = getConfigCache<PagesConfigCache>(
 		PAGES_CONFIG_CACHE_FILENAME
 	);
-	const accountId =
-		getCloudflareAccountIdFromEnv() ?? (await requireAuth(configCache));
+	const envAccountId = getCloudflareAccountIdFromEnv();
+	const accountId = await requireAuth({
+		...configCache,
+		...(envAccountId ? { account_id: envAccountId } : {}),
+	});
 
 	const projectName =
 		cliProjectName ?? config?.name ?? configCache.project_name;
diff --git a/packages/wrangler/src/queues/cli/commands/consumer/http-pull/add.ts b/packages/wrangler/src/queues/cli/commands/consumer/http-pull/add.ts
index 19ed832a4e..3e5646659e 100644
--- a/packages/wrangler/src/queues/cli/commands/consumer/http-pull/add.ts
+++ b/packages/wrangler/src/queues/cli/commands/consumer/http-pull/add.ts
@@ -10,6 +10,7 @@ export const queuesConsumerHttpAddCommand = createCommand({
 		owner: "Product: Queues",
 		status: "stable",
 	},
+	behaviour: { supportTemporary: true },
 	args: {
 		"queue-name": {
 			type: "string",
diff --git a/packages/wrangler/src/queues/cli/commands/consumer/http-pull/list.ts b/packages/wrangler/src/queues/cli/commands/consumer/http-pull/list.ts
index 69fd55d5c5..709905d3c5 100644
--- a/packages/wrangler/src/queues/cli/commands/consumer/http-pull/list.ts
+++ b/packages/wrangler/src/queues/cli/commands/consumer/http-pull/list.ts
@@ -22,6 +22,7 @@ export const queuesConsumerHttpListCommand = createCommand({
 		status: "stable",
 	},
 	behaviour: {
+		supportTemporary: true,
 		printBanner: (args) => !args.json,
 	},
 	args: {
diff --git a/packages/wrangler/src/queues/cli/commands/consumer/http-pull/remove.ts b/packages/wrangler/src/queues/cli/commands/consumer/http-pull/remove.ts
index 783ddafa0f..5612b115f3 100644
--- a/packages/wrangler/src/queues/cli/commands/consumer/http-pull/remove.ts
+++ b/packages/wrangler/src/queues/cli/commands/consumer/http-pull/remove.ts
@@ -8,6 +8,7 @@ export const queuesConsumerHttpRemoveCommand = createCommand({
 		owner: "Product: Queues",
 		status: "stable",
 	},
+	behaviour: { supportTemporary: true },
 	args: {
 		"queue-name": {
 			type: "string",
diff --git a/packages/wrangler/src/queues/cli/commands/consumer/list.ts b/packages/wrangler/src/queues/cli/commands/consumer/list.ts
index 217e2f28dc..e1ff0695f7 100644
--- a/packages/wrangler/src/queues/cli/commands/consumer/list.ts
+++ b/packages/wrangler/src/queues/cli/commands/consumer/list.ts
@@ -11,6 +11,7 @@ export const queuesConsumerListCommand = createCommand({
 		status: "stable",
 	},
 	behaviour: {
+		supportTemporary: true,
 		printBanner: (args) => !args.json,
 	},
 	args: {
diff --git a/packages/wrangler/src/queues/cli/commands/consumer/worker/add.ts b/packages/wrangler/src/queues/cli/commands/consumer/worker/add.ts
index 43dea6881a..6510eb8129 100644
--- a/packages/wrangler/src/queues/cli/commands/consumer/worker/add.ts
+++ b/packages/wrangler/src/queues/cli/commands/consumer/worker/add.ts
@@ -9,6 +9,7 @@ export const queuesConsumerAddCommand = createCommand({
 		owner: "Product: Queues",
 		status: "stable",
 	},
+	behaviour: { supportTemporary: true },
 	args: {
 		"queue-name": {
 			type: "string",
diff --git a/packages/wrangler/src/queues/cli/commands/consumer/worker/list.ts b/packages/wrangler/src/queues/cli/commands/consumer/worker/list.ts
index e61971763e..6f145b1a50 100644
--- a/packages/wrangler/src/queues/cli/commands/consumer/worker/list.ts
+++ b/packages/wrangler/src/queues/cli/commands/consumer/worker/list.ts
@@ -23,6 +23,7 @@ export const queuesConsumerWorkerListCommand = createCommand({
 		status: "stable",
 	},
 	behaviour: {
+		supportTemporary: true,
 		printBanner: (args) => !args.json,
 	},
 	args: {
diff --git a/packages/wrangler/src/queues/cli/commands/consumer/worker/remove.ts b/packages/wrangler/src/queues/cli/commands/consumer/worker/remove.ts
index 262f927a00..2b088d0cb3 100644
--- a/packages/wrangler/src/queues/cli/commands/consumer/worker/remove.ts
+++ b/packages/wrangler/src/queues/cli/commands/consumer/worker/remove.ts
@@ -8,6 +8,7 @@ export const queuesConsumerRemoveCommand = createCommand({
 		owner: "Product: Queues",
 		status: "stable",
 	},
+	behaviour: { supportTemporary: true },
 	args: {
 		"queue-name": {
 			type: "string",
diff --git a/packages/wrangler/src/queues/cli/commands/create.ts b/packages/wrangler/src/queues/cli/commands/create.ts
index 991470fb35..5be434fc87 100644
--- a/packages/wrangler/src/queues/cli/commands/create.ts
+++ b/packages/wrangler/src/queues/cli/commands/create.ts
@@ -22,6 +22,7 @@ export const queuesCreateCommand = createCommand({
 		owner: "Product: Queues",
 		status: "stable",
 	},
+	behaviour: { supportTemporary: true },
 	args: {
 		name: {
 			type: "string",
diff --git a/packages/wrangler/src/queues/cli/commands/delete.ts b/packages/wrangler/src/queues/cli/commands/delete.ts
index 623c48d1d1..903546cd1a 100644
--- a/packages/wrangler/src/queues/cli/commands/delete.ts
+++ b/packages/wrangler/src/queues/cli/commands/delete.ts
@@ -8,6 +8,7 @@ export const queuesDeleteCommand = createCommand({
 		owner: "Product: Queues",
 		status: "stable",
 	},
+	behaviour: { supportTemporary: true },
 	args: {
 		name: {
 			type: "string",
diff --git a/packages/wrangler/src/queues/cli/commands/info.ts b/packages/wrangler/src/queues/cli/commands/info.ts
index 7c72352f53..e65aad38e6 100644
--- a/packages/wrangler/src/queues/cli/commands/info.ts
+++ b/packages/wrangler/src/queues/cli/commands/info.ts
@@ -10,6 +10,7 @@ export const queuesInfoCommand = createCommand({
 		owner: "Product: Queues",
 		status: "stable",
 	},
+	behaviour: { supportTemporary: true },
 	args: {
 		name: {
 			type: "string",
diff --git a/packages/wrangler/src/queues/cli/commands/list.ts b/packages/wrangler/src/queues/cli/commands/list.ts
index ade912cf1c..335e4ce515 100644
--- a/packages/wrangler/src/queues/cli/commands/list.ts
+++ b/packages/wrangler/src/queues/cli/commands/list.ts
@@ -8,6 +8,7 @@ export const queuesListCommand = createCommand({
 		status: "stable",
 		owner: "Product: Queues",
 	},
+	behaviour: { supportTemporary: true },
 	args: {
 		page: {
 			type: "number",
diff --git a/packages/wrangler/src/queues/cli/commands/pause-resume.ts b/packages/wrangler/src/queues/cli/commands/pause-resume.ts
index 1add6a2ce0..4341c055a3 100644
--- a/packages/wrangler/src/queues/cli/commands/pause-resume.ts
+++ b/packages/wrangler/src/queues/cli/commands/pause-resume.ts
@@ -11,6 +11,7 @@ export const queuesPauseCommand = createCommand({
 		owner: "Product: Queues",
 		status: "stable",
 	},
+	behaviour: { supportTemporary: true },
 	args: {
 		name: {
 			type: "string",
@@ -30,6 +31,7 @@ export const queuesResumeCommand = createCommand({
 		owner: "Product: Queues",
 		status: "stable",
 	},
+	behaviour: { supportTemporary: true },
 	args: {
 		name: {
 			type: "string",
diff --git a/packages/wrangler/src/queues/cli/commands/purge.ts b/packages/wrangler/src/queues/cli/commands/purge.ts
index 82c2f9f937..5eaffbd183 100644
--- a/packages/wrangler/src/queues/cli/commands/purge.ts
+++ b/packages/wrangler/src/queues/cli/commands/purge.ts
@@ -11,6 +11,7 @@ export const queuesPurgeCommand = createCommand({
 		owner: "Product: Queues",
 		status: "stable",
 	},
+	behaviour: { supportTemporary: true },
 	args: {
 		name: {
 			type: "string",
diff --git a/packages/wrangler/src/queues/cli/commands/subscription/create.ts b/packages/wrangler/src/queues/cli/commands/subscription/create.ts
index 321ce45bed..296d17b2eb 100644
--- a/packages/wrangler/src/queues/cli/commands/subscription/create.ts
+++ b/packages/wrangler/src/queues/cli/commands/subscription/create.ts
@@ -85,6 +85,7 @@ export const queuesSubscriptionCreateCommand = createCommand({
 		owner: "Product: Queues",
 		status: "stable",
 	},
+	behaviour: { supportTemporary: true },
 	positionalArgs: ["queue"],
 	args: {
 		queue: {
diff --git a/packages/wrangler/src/queues/cli/commands/subscription/delete.ts b/packages/wrangler/src/queues/cli/commands/subscription/delete.ts
index 57dee666a0..7df6ccc7c3 100644
--- a/packages/wrangler/src/queues/cli/commands/subscription/delete.ts
+++ b/packages/wrangler/src/queues/cli/commands/subscription/delete.ts
@@ -12,6 +12,7 @@ export const queuesSubscriptionDeleteCommand = createCommand({
 		owner: "Product: Queues",
 		status: "stable",
 	},
+	behaviour: { supportTemporary: true },
 	positionalArgs: ["queue"],
 	args: {
 		queue: {
diff --git a/packages/wrangler/src/queues/cli/commands/subscription/get.ts b/packages/wrangler/src/queues/cli/commands/subscription/get.ts
index 32b733d68f..b2dd7ba0cb 100644
--- a/packages/wrangler/src/queues/cli/commands/subscription/get.ts
+++ b/packages/wrangler/src/queues/cli/commands/subscription/get.ts
@@ -11,6 +11,7 @@ export const queuesSubscriptionGetCommand = createCommand({
 		status: "stable",
 	},
 	behaviour: {
+		supportTemporary: true,
 		printBanner: (args) => !args.json,
 	},
 	positionalArgs: ["queue"],
diff --git a/packages/wrangler/src/queues/cli/commands/subscription/list.ts b/packages/wrangler/src/queues/cli/commands/subscription/list.ts
index 222a805565..8ab8583c2f 100644
--- a/packages/wrangler/src/queues/cli/commands/subscription/list.ts
+++ b/packages/wrangler/src/queues/cli/commands/subscription/list.ts
@@ -10,6 +10,7 @@ export const queuesSubscriptionListCommand = createCommand({
 		status: "stable",
 	},
 	behaviour: {
+		supportTemporary: true,
 		printBanner: (args) => !args.json,
 	},
 	positionalArgs: ["queue"],
diff --git a/packages/wrangler/src/queues/cli/commands/subscription/update.ts b/packages/wrangler/src/queues/cli/commands/subscription/update.ts
index e7d21fbde8..dfa132f8d4 100644
--- a/packages/wrangler/src/queues/cli/commands/subscription/update.ts
+++ b/packages/wrangler/src/queues/cli/commands/subscription/update.ts
@@ -13,6 +13,7 @@ export const queuesSubscriptionUpdateCommand = createCommand({
 		status: "stable",
 	},
 	behaviour: {
+		supportTemporary: true,
 		printBanner: (args) => !args.json,
 	},
 	positionalArgs: ["queue"],
diff --git a/packages/wrangler/src/queues/cli/commands/update.ts b/packages/wrangler/src/queues/cli/commands/update.ts
index d06c8a7159..c7063df244 100644
--- a/packages/wrangler/src/queues/cli/commands/update.ts
+++ b/packages/wrangler/src/queues/cli/commands/update.ts
@@ -17,6 +17,7 @@ export const queuesUpdateCommand = createCommand({
 		owner: "Product: Queues",
 		status: "stable",
 	},
+	behaviour: { supportTemporary: true },
 	args: {
 		name: {
 			type: "string",
diff --git a/packages/wrangler/src/secret/index.ts b/packages/wrangler/src/secret/index.ts
index 46186b327d..851ff32e58 100644
--- a/packages/wrangler/src/secret/index.ts
+++ b/packages/wrangler/src/secret/index.ts
@@ -99,6 +99,7 @@ export const secretPutCommand = createCommand({
 	},
 	positionalArgs: ["key"],
 	behaviour: {
+		supportTemporary: true,
 		warnIfMultipleEnvsConfiguredButNoneSpecified: true,
 		suggestSkillsAfterHandler: true,
 	},
@@ -230,6 +231,7 @@ export const secretDeleteCommand = createCommand({
 	},
 	positionalArgs: ["key"],
 	behaviour: {
+		supportTemporary: true,
 		warnIfMultipleEnvsConfiguredButNoneSpecified: true,
 		suggestSkillsAfterHandler: true,
 	},
@@ -330,6 +332,7 @@ export const secretListCommand = createCommand({
 		},
 	},
 	behaviour: {
+		supportTemporary: true,
 		printBanner: (args) => args.format === "pretty",
 		suggestSkillsAfterHandler: (args) => args.format === "pretty",
 	},
@@ -433,6 +436,7 @@ export const secretBulkCommand = createCommand({
 	},
 	positionalArgs: ["file"],
 	behaviour: {
+		supportTemporary: true,
 		warnIfMultipleEnvsConfiguredButNoneSpecified: true,
 		suggestSkillsAfterHandler: true,
 	},
diff --git a/packages/wrangler/src/tail/index.ts b/packages/wrangler/src/tail/index.ts
index ef631f4f8a..d0924708ca 100644
--- a/packages/wrangler/src/tail/index.ts
+++ b/packages/wrangler/src/tail/index.ts
@@ -90,6 +90,7 @@ export const tailCommand = createCommand({
 		},
 	},
 	behaviour: {
+		supportTemporary: true,
 		printBanner: false,
 	},
 	async handler(args, { config }) {
diff --git a/packages/wrangler/src/triggers/index.ts b/packages/wrangler/src/triggers/index.ts
index d7fe8ddf7e..8b93cb34fd 100644
--- a/packages/wrangler/src/triggers/index.ts
+++ b/packages/wrangler/src/triggers/index.ts
@@ -59,6 +59,7 @@ export const triggersDeployCommand = createCommand({
 		},
 	},
 	behaviour: {
+		supportTemporary: true,
 		warnIfMultipleEnvsConfiguredButNoneSpecified: true,
 		suggestSkillsAfterHandler: true,
 	},
diff --git a/packages/wrangler/src/user/auth-config-file.ts b/packages/wrangler/src/user/auth-config-file.ts
index be3bd0ab1a..efd1651f48 100644
--- a/packages/wrangler/src/user/auth-config-file.ts
+++ b/packages/wrangler/src/user/auth-config-file.ts
@@ -1,4 +1,10 @@
-import { chmodSync, mkdirSync, rmSync, writeFileSync } from "node:fs";
+import {
+	chmodSync,
+	existsSync,
+	mkdirSync,
+	rmSync,
+	writeFileSync,
+} from "node:fs";
 import path from "node:path";
 import {
 	getCloudflareApiEnvironmentFromEnv,
@@ -9,9 +15,45 @@ import {
 import TOML from "smol-toml";
 import type {
 	AuthConfigStorage,
+	ConfigStorage,
 	UserAuthConfig,
 } from "@cloudflare/workers-auth";
 
+/**
+ * A TOML-file-on-disk storage backend, parameterised by the path it reads and
+ * writes. Shared by the OAuth auth-config store ({@link defaultAuthConfigStorage})
+ * and the temporary-preview-account store (`defaultTemporaryAccountStorage`) so
+ * both get identical owner-only permission handling.
+ *
+ * `read()` throws when the file is missing or cannot be parsed — callers treat a
+ * throw as "nothing stored". Files are written with mode `0o600` on creation and
+ * re-`chmod`'d on every save (the `mode` option only applies on creation) so
+ * other local users on shared hosts can't read the stored credentials.
+ */
+export function createTomlFileStorage<T extends object>(
+	getPath: () => string
+): ConfigStorage<T> {
+	return {
+		read: () => parseTOML(readFileSync(getPath())) as T,
+		write(config) {
+			const configPath = getPath();
+			mkdirSync(path.dirname(configPath), { recursive: true });
+			writeFileSync(configPath, TOML.stringify(config), {
+				encoding: "utf-8",
+				mode: 0o600,
+			});
+			chmodSync(configPath, 0o600);
+		},
+		clear() {
+			const configPath = getPath();
+			const existed = existsSync(configPath);
+			rmSync(configPath, { force: true });
+			return existed;
+		},
+		path: getPath,
+	};
+}
+
 /**
  * Wrangler's default `AuthConfigStorage`: a TOML file on disk, located under
  * the global Wrangler config directory.
@@ -20,12 +62,7 @@ import type {
  * `readStoredAuthState`), which no longer ships a default of its own.
  */
 export function defaultAuthConfigStorage(): AuthConfigStorage {
-	return {
-		read: readAuthConfigFile,
-		write: writeAuthConfigFile,
-		clear: () => rmSync(getAuthConfigFilePath()),
-		path: getAuthConfigFilePath,
-	};
+	return createTomlFileStorage<UserAuthConfig>(getAuthConfigFilePath);
 }
 
 /**
@@ -55,22 +92,7 @@ export function getAuthConfigFilePath(): string {
  * purging (e.g. via the `OAuthFlowContext.purgeOnLoginOrLogout` hook).
  */
 export function writeAuthConfigFile(config: UserAuthConfig): void {
-	const configPath = getAuthConfigFilePath();
-
-	mkdirSync(path.dirname(configPath), {
-		recursive: true,
-	});
-	// Write with mode 0o600 on creation and re-`chmod` on every save so
-	// other local users on shared hosts can't read the OAuth tokens.
-	// `writeFileSync`'s `mode` option only applies when the file is
-	// being created — the explicit `chmodSync` ensures that pre-existing
-	// files (e.g. written by an older Wrangler version with the process
-	// umask) get tightened on the next save too.
-	writeFileSync(configPath, TOML.stringify(config), {
-		encoding: "utf-8",
-		mode: 0o600,
-	});
-	chmodSync(configPath, 0o600);
+	createTomlFileStorage<UserAuthConfig>(getAuthConfigFilePath).write(config);
 }
 
 /**
@@ -80,5 +102,5 @@ export function writeAuthConfigFile(config: UserAuthConfig): void {
  * typically catch this and treat the failure as "not logged in via local OAuth".
  */
 export function readAuthConfigFile(): UserAuthConfig {
-	return parseTOML(readFileSync(getAuthConfigFilePath())) as UserAuthConfig;
+	return createTomlFileStorage<UserAuthConfig>(getAuthConfigFilePath).read();
 }
diff --git a/packages/wrangler/src/user/temporary-account-path.ts b/packages/wrangler/src/user/temporary-account-path.ts
new file mode 100644
index 0000000000..4fbd0eab30
--- /dev/null
+++ b/packages/wrangler/src/user/temporary-account-path.ts
@@ -0,0 +1,25 @@
+import path from "node:path";
+import {
+	getCloudflareApiEnvironmentFromEnv,
+	getGlobalWranglerConfigPath,
+} from "@cloudflare/workers-utils";
+
+function getTemporaryAccountConfigFile(): string {
+	const environment = getCloudflareApiEnvironmentFromEnv();
+	return environment === "production"
+		? "wrangler-temporary-account.toml"
+		: `wrangler-temporary-account.${environment}.toml`;
+}
+
+/**
+ * Absolute path to wrangler's temporary-preview-account cache file, under the
+ * global Wrangler config directory and scoped to the current
+ * `WRANGLER_API_ENVIRONMENT`. Paired with `createTomlFileStorage` to build the
+ * `TemporaryAccountStorage` injected into the OAuth flow.
+ */
+export function getTemporaryPreviewAccountConfigPath(): string {
+	return path.join(
+		getGlobalWranglerConfigPath(),
+		getTemporaryAccountConfigFile()
+	);
+}
diff --git a/packages/wrangler/src/user/temporary-terms.ts b/packages/wrangler/src/user/temporary-terms.ts
new file mode 100644
index 0000000000..4db5b70a1b
--- /dev/null
+++ b/packages/wrangler/src/user/temporary-terms.ts
@@ -0,0 +1,20 @@
+import { prompt } from "../dialogs";
+import { isNonInteractiveOrCI } from "../is-interactive";
+import { logger } from "../logger";
+
+export async function ensureTemporaryTermsAccepted(
+	question: string,
+	notice: string
+): Promise<boolean> {
+	if (isNonInteractiveOrCI()) {
+		logger.log(notice);
+		return true;
+	}
+
+	const answer = await prompt(question);
+	if (typeof answer === "string" && answer.trim().toLowerCase() === "yes") {
+		return true;
+	}
+
+	return false;
+}
diff --git a/packages/wrangler/src/user/user.ts b/packages/wrangler/src/user/user.ts
index 62c8e3ee07..c885fcf74e 100644
--- a/packages/wrangler/src/user/user.ts
+++ b/packages/wrangler/src/user/user.ts
@@ -12,21 +12,28 @@
 
 import assert from "node:assert";
 import {
-	getAPIToken as getAPITokenShared,
 	getAuthFromEnv as getAuthFromEnvShared,
 	readStoredAuthState,
-	requireApiToken as requireApiTokenShared,
 } from "@cloudflare/workers-auth";
 import { createOAuthFlow } from "@cloudflare/workers-auth";
-import { configFileName, UserError } from "@cloudflare/workers-utils";
+import {
+	configFileName,
+	getCloudflareComplianceRegion,
+	UserError,
+} from "@cloudflare/workers-utils";
 import ci from "ci-info";
+import { formatDistanceToNowStrict } from "date-fns";
+import { dedent } from "ts-dedent";
 import { getConfigCache, saveToConfigCache } from "../config-cache";
 import { purgeConfigCaches } from "../config-cache";
 import { NoDefaultValueProvided, select } from "../dialogs";
 import { isNonInteractiveOrCI } from "../is-interactive";
 import { logger } from "../logger";
 import openInBrowser from "../open-in-browser";
-import { defaultAuthConfigStorage } from "./auth-config-file";
+import {
+	createTomlFileStorage,
+	defaultAuthConfigStorage,
+} from "./auth-config-file";
 import {
 	getClientIdFromEnv,
 	getCloudflareAccountIdFromEnv,
@@ -34,10 +41,13 @@ import {
 import { fetchAllAccounts } from "./fetch-accounts";
 import { generateAuthUrl, OAUTH_CALLBACK_URL } from "./generate-auth-url";
 import { generateRandomState } from "./generate-random-state";
+import { getTemporaryPreviewAccountConfigPath } from "./temporary-account-path";
+import { ensureTemporaryTermsAccepted } from "./temporary-terms";
 import type { Account } from "./shared";
 import type {
 	LoginOrRefreshResult,
 	LoginProps,
+	TemporaryPreviewAccount,
 } from "@cloudflare/workers-auth";
 import type {
 	ApiCredentials,
@@ -84,10 +94,39 @@ const oauthFlow = createOAuthFlow({
 	consent: WRANGLER_CONSENT_PAGES,
 	redirectUri: OAUTH_CALLBACK_URL,
 	storage: authConfigStorage,
+	allowGlobalAuthKey: true,
+	temporary: {
+		storage: createTomlFileStorage<TemporaryPreviewAccount>(
+			getTemporaryPreviewAccountConfigPath
+		),
+		prompt: ensureTemporaryTermsAccepted,
+	},
 	generateAuthUrl,
 	generateRandomState,
 });
 
+/**
+ * Mark whether `--temporary` is permitted for the current invocation.
+ */
+export function setTemporaryAllowed(allowed: boolean): void {
+	oauthFlow.setTemporaryAllowed(allowed);
+}
+
+function logTemporaryPreviewAccount(
+	temporaryPreviewAccount: TemporaryPreviewAccount,
+	cached: boolean
+): void {
+	const claimExpiresAt = new Date(temporaryPreviewAccount.claim.expiresAt);
+	logger.log(
+		dedent`
+			Temporary account ready:
+				Account: ${temporaryPreviewAccount.account.name} (${cached ? "reused" : "created"})
+				Claim within: ${formatDistanceToNowStrict(claimExpiresAt)}
+				Claim URL: ${temporaryPreviewAccount.claim.url}
+		`
+	);
+}
+
 /**
  * Try to read API credentials from environment variables.
  *
@@ -201,20 +240,14 @@ export function printScopes(scopes: Scope[]) {
 // ---------------------------------------------------------------------------
 
 export function getAPIToken(): ApiCredentials | undefined {
-	return getAPITokenShared({
-		warningLogger: logger,
-		storage: authConfigStorage,
-	});
+	return oauthFlow.getAPIToken();
 }
 
 /**
  * Throw an error if there is no API token available.
  */
 export function requireApiToken(): ApiCredentials {
-	return requireApiTokenShared({
-		warningLogger: logger,
-		storage: authConfigStorage,
-	});
+	return oauthFlow.requireApiToken();
 }
 
 // ---------------------------------------------------------------------------
@@ -266,6 +299,10 @@ export async function loginOrRefreshIfRequired(
 	complianceConfig: ComplianceConfig,
 	props?: WranglerLoginProps
 ): Promise<LoginOrRefreshResult> {
+	if (oauthFlow.getActiveTemporaryAccount()) {
+		return { loggedIn: true };
+	}
+
 	return oauthFlow.loginOrRefreshIfRequired(
 		withDefaultScopes(complianceConfig, props)
 	);
@@ -306,6 +343,13 @@ export { PKCE_CHARSET } from "@cloudflare/workers-auth";
 export function getActiveAccountId(config: {
 	account_id?: string;
 }): string | undefined {
+	// When operating as a temporary preview account, its id is the whole
+	// identity and takes precedence over config/env/cache.
+	const temporaryAccount = oauthFlow.getActiveTemporaryAccount();
+	if (temporaryAccount) {
+		return temporaryAccount.account.id;
+	}
+
 	if (config.account_id) {
 		return config.account_id;
 	}
@@ -405,6 +449,35 @@ export async function requireAuth(
 		account_id?: string;
 	}
 ): Promise<string> {
+	if (oauthFlow.isTemporaryAllowed()) {
+		if (getCloudflareComplianceRegion(config) !== "public") {
+			throw new UserError(
+				"Temporary accounts aren't available when the compliance region is not set to public.",
+				{
+					telemetryMessage:
+						"user temporary account unavailable in compliance region",
+				}
+			);
+		}
+
+		// `--temporary` is only for unauthenticated use. If any credentials are
+		// already available (env, global key, or a stored OAuth token), refuse
+		// rather than silently provisioning a throwaway account alongside them.
+		if (getAPIToken()) {
+			throw new UserError(
+				"You're already authenticated with Cloudflare, so `--temporary` can't be used. Temporary preview accounts are only for unauthenticated use. Either remove `--temporary` to use your existing account, or log out (and unset CLOUDFLARE_API_TOKEN) first.",
+				{
+					telemetryMessage: "user temporary account already authenticated",
+				}
+			);
+		}
+
+		const { account: temporaryPreviewAccount, cached } =
+			await oauthFlow.activateTemporaryAccount();
+		logTemporaryPreviewAccount(temporaryPreviewAccount, cached);
+		return temporaryPreviewAccount.account.id;
+	}
+
 	const result = await loginOrRefreshIfRequired(config);
 	if (!result.loggedIn) {
 		if (
@@ -422,6 +495,7 @@ export async function requireAuth(
 			});
 		}
 	}
+
 	const accountId = await getOrSelectAccountId(config);
 	if (!accountId) {
 		throw new UserError("No account id found, quitting...", {
diff --git a/packages/wrangler/src/versions/deploy.ts b/packages/wrangler/src/versions/deploy.ts
index 549308ecd6..362401d2a6 100644
--- a/packages/wrangler/src/versions/deploy.ts
+++ b/packages/wrangler/src/versions/deploy.ts
@@ -41,6 +41,7 @@ export const versionsDeployCommand = createCommand({
 		status: "stable",
 	},
 	behaviour: {
+		supportTemporary: true,
 		useConfigRedirectIfAvailable: true,
 		warnIfMultipleEnvsConfiguredButNoneSpecified: true,
 		suggestSkillsAfterHandler: true,
diff --git a/packages/wrangler/src/versions/deployments/list.ts b/packages/wrangler/src/versions/deployments/list.ts
index 805afbd5a3..1e448f35e8 100644
--- a/packages/wrangler/src/versions/deployments/list.ts
+++ b/packages/wrangler/src/versions/deployments/list.ts
@@ -31,6 +31,7 @@ export const deploymentsListCommand = createCommand({
 		},
 	},
 	behaviour: {
+		supportTemporary: true,
 		printBanner: (args) => !args.json,
 		suggestSkillsAfterHandler: (args) => !args.json,
 	},
diff --git a/packages/wrangler/src/versions/deployments/status.ts b/packages/wrangler/src/versions/deployments/status.ts
index 095e80d902..66f2ef9480 100644
--- a/packages/wrangler/src/versions/deployments/status.ts
+++ b/packages/wrangler/src/versions/deployments/status.ts
@@ -31,6 +31,7 @@ export const deploymentsStatusCommand = createCommand({
 		},
 	},
 	behaviour: {
+		supportTemporary: true,
 		printBanner: (args) => !args.json,
 		suggestSkillsAfterHandler: (args) => !args.json,
 	},
diff --git a/packages/wrangler/src/versions/deployments/view.ts b/packages/wrangler/src/versions/deployments/view.ts
index f8fecabbfb..1b0ec8d555 100644
--- a/packages/wrangler/src/versions/deployments/view.ts
+++ b/packages/wrangler/src/versions/deployments/view.ts
@@ -9,6 +9,7 @@ export const deploymentsViewCommand = createCommand({
 		hidden: true,
 	},
 	behaviour: {
+		supportTemporary: true,
 		suggestSkillsAfterHandler: true,
 	},
 	args: {
diff --git a/packages/wrangler/src/versions/list.ts b/packages/wrangler/src/versions/list.ts
index 43baf59166..160d463916 100644
--- a/packages/wrangler/src/versions/list.ts
+++ b/packages/wrangler/src/versions/list.ts
@@ -17,6 +17,7 @@ export const versionsListCommand = createCommand({
 		status: "stable",
 	},
 	behaviour: {
+		supportTemporary: true,
 		printBanner: (args) => !args.json,
 		suggestSkillsAfterHandler: (args) => !args.json,
 	},
diff --git a/packages/wrangler/src/versions/rollback/index.ts b/packages/wrangler/src/versions/rollback/index.ts
index 222abb57d7..44b26800a2 100644
--- a/packages/wrangler/src/versions/rollback/index.ts
+++ b/packages/wrangler/src/versions/rollback/index.ts
@@ -44,6 +44,7 @@ export const versionsRollbackCommand = createCommand({
 		category: "Compute & AI",
 	},
 	behaviour: {
+		supportTemporary: true,
 		suggestSkillsAfterHandler: true,
 	},
 	handler: async function handleRollback(args, { config }) {
diff --git a/packages/wrangler/src/versions/secrets/bulk.ts b/packages/wrangler/src/versions/secrets/bulk.ts
index 08fefb2733..acdec8180f 100644
--- a/packages/wrangler/src/versions/secrets/bulk.ts
+++ b/packages/wrangler/src/versions/secrets/bulk.ts
@@ -16,6 +16,7 @@ export const versionsSecretBulkCommand = createCommand({
 		status: "stable",
 	},
 	behaviour: {
+		supportTemporary: true,
 		printConfigWarnings: false,
 		warnIfMultipleEnvsConfiguredButNoneSpecified: true,
 		suggestSkillsAfterHandler: true,
diff --git a/packages/wrangler/src/versions/secrets/delete.ts b/packages/wrangler/src/versions/secrets/delete.ts
index 8c54fae33a..e45a9fd8d4 100644
--- a/packages/wrangler/src/versions/secrets/delete.ts
+++ b/packages/wrangler/src/versions/secrets/delete.ts
@@ -16,6 +16,7 @@ export const versionsSecretDeleteCommand = createCommand({
 		status: "stable",
 	},
 	behaviour: {
+		supportTemporary: true,
 		printConfigWarnings: false,
 		warnIfMultipleEnvsConfiguredButNoneSpecified: true,
 		suggestSkillsAfterHandler: true,
diff --git a/packages/wrangler/src/versions/secrets/list.ts b/packages/wrangler/src/versions/secrets/list.ts
index 8b3b9d551b..f89d650e54 100644
--- a/packages/wrangler/src/versions/secrets/list.ts
+++ b/packages/wrangler/src/versions/secrets/list.ts
@@ -15,6 +15,7 @@ export const versionsSecretsListCommand = createCommand({
 		status: "stable",
 	},
 	behaviour: {
+		supportTemporary: true,
 		printConfigWarnings: false,
 		suggestSkillsAfterHandler: true,
 	},
diff --git a/packages/wrangler/src/versions/secrets/put.ts b/packages/wrangler/src/versions/secrets/put.ts
index 350a415c1e..aa2177393f 100644
--- a/packages/wrangler/src/versions/secrets/put.ts
+++ b/packages/wrangler/src/versions/secrets/put.ts
@@ -17,6 +17,7 @@ export const versionsSecretPutCommand = createCommand({
 		status: "stable",
 	},
 	behaviour: {
+		supportTemporary: true,
 		printConfigWarnings: false,
 		warnIfMultipleEnvsConfiguredButNoneSpecified: true,
 		suggestSkillsAfterHandler: true,
diff --git a/packages/wrangler/src/versions/upload.ts b/packages/wrangler/src/versions/upload.ts
index 7a5adae2a2..46a33a190c 100644
--- a/packages/wrangler/src/versions/upload.ts
+++ b/packages/wrangler/src/versions/upload.ts
@@ -33,6 +33,7 @@ export const versionsUploadCommand = createCommand({
 		},
 	},
 	behaviour: {
+		supportTemporary: true,
 		useConfigRedirectIfAvailable: true,
 		overrideExperimentalFlags: (args) => ({
 			MULTIWORKER: false,
diff --git a/packages/wrangler/src/versions/view.ts b/packages/wrangler/src/versions/view.ts
index 2c01816211..b6070fff17 100644
--- a/packages/wrangler/src/versions/view.ts
+++ b/packages/wrangler/src/versions/view.ts
@@ -18,6 +18,7 @@ export const versionsViewCommand = createCommand({
 		status: "stable",
 	},
 	behaviour: {
+		supportTemporary: true,
 		printBanner: (args) => !args.json,
 		suggestSkillsAfterHandler: (args) => !args.json,
 	},

From e3fce14228f6e064d5d7408508107774fa38c296 Mon Sep 17 00:00:00 2001
From: emily-shen <69125074+emily-shen@users.noreply.github.com>
Date: Fri, 12 Jun 2026 16:55:29 +0100
Subject: [PATCH 4/4] re-export `ConfigSchema` and `convertToWranglerConfig`
 from deploy-helpers (#14265)

Co-authored-by: devin-ai-integration[bot] <158243242+devin-ai-integration[bot]@users.noreply.github.com>
---
 .../bundle-private-deploy-helpers-deps.md      |  7 +++++++
 .changeset/tidy-clouds-config.md               |  7 +++++++
 packages/config/tsdown.config.ts               |  4 ++++
 packages/deploy-helpers/package.json           | 16 +++++++++++++---
 packages/deploy-helpers/scripts/deps.ts        |  7 +++++--
 packages/deploy-helpers/src/config.ts          |  2 ++
 packages/deploy-helpers/src/index.ts           |  1 +
 packages/deploy-helpers/tsup.config.ts         |  8 ++++++++
 .../wrangler/src/experimental-config/load.ts   |  5 ++---
 pnpm-lock.yaml                                 | 18 ++++++++++++------
 10 files changed, 61 insertions(+), 14 deletions(-)
 create mode 100644 .changeset/bundle-private-deploy-helpers-deps.md
 create mode 100644 .changeset/tidy-clouds-config.md
 create mode 100644 packages/deploy-helpers/src/config.ts

diff --git a/.changeset/bundle-private-deploy-helpers-deps.md b/.changeset/bundle-private-deploy-helpers-deps.md
new file mode 100644
index 0000000000..b0b6df960f
--- /dev/null
+++ b/.changeset/bundle-private-deploy-helpers-deps.md
@@ -0,0 +1,7 @@
+---
+"@cloudflare/deploy-helpers": patch
+---
+
+Bundle private internal dependencies in deploy helpers
+
+`@cloudflare/deploy-helpers` no longer declares private workspace packages as runtime dependencies, so installing the package from npm does not require unpublished internal packages.
diff --git a/.changeset/tidy-clouds-config.md b/.changeset/tidy-clouds-config.md
new file mode 100644
index 0000000000..8bbbb35fc1
--- /dev/null
+++ b/.changeset/tidy-clouds-config.md
@@ -0,0 +1,7 @@
+---
+"@cloudflare/deploy-helpers": minor
+---
+
+Expose Cloudflare config conversion utilities from deploy helpers
+
+`@cloudflare/deploy-helpers` now re-exports `ConfigSchema` and `convertToWranglerConfig` from the internal `@cloudflare/config` package, so consumers can parse and convert Cloudflare config files without depending on the unpublished package directly.
diff --git a/packages/config/tsdown.config.ts b/packages/config/tsdown.config.ts
index 8892471379..3a4a9d4f91 100644
--- a/packages/config/tsdown.config.ts
+++ b/packages/config/tsdown.config.ts
@@ -9,4 +9,8 @@ export default defineConfig({
 	outDir: "dist",
 	dts: true,
 	tsconfig: "tsconfig.json",
+	// Keep zod external so consumers that bundle this package (wrangler,
+	// deploy-helpers, vite-plugin) share a single zod copy instead of inlining
+	// one per consumed entry point.
+	external: [/^zod(\/.*)?$/],
 });
diff --git a/packages/deploy-helpers/package.json b/packages/deploy-helpers/package.json
index 4ea4e1ca94..fdad76607c 100644
--- a/packages/deploy-helpers/package.json
+++ b/packages/deploy-helpers/package.json
@@ -38,8 +38,6 @@
 	},
 	"dependencies": {
 		"@cloudflare/cli-shared-helpers": "workspace:*",
-		"@cloudflare/containers-shared": "workspace:*",
-		"@cloudflare/workers-shared": "workspace:*",
 		"@cloudflare/workers-utils": "workspace:*",
 		"blake3-wasm": "2.1.5",
 		"chalk": "catalog:default",
@@ -51,6 +49,9 @@
 		"undici": "catalog:default"
 	},
 	"devDependencies": {
+		"@cloudflare/config": "workspace:*",
+		"@cloudflare/containers-shared": "workspace:*",
+		"@cloudflare/workers-shared": "workspace:*",
 		"@cloudflare/workers-tsconfig": "workspace:*",
 		"@cspotcode/source-map-support": "0.8.1",
 		"@types/command-exists": "^1.2.0",
@@ -63,7 +64,16 @@
 		"ts-dedent": "^2.2.0",
 		"tsup": "8.3.0",
 		"typescript": "catalog:default",
-		"vitest": "catalog:default"
+		"vitest": "catalog:default",
+		"zod": "^4.4.3"
+	},
+	"peerDependencies": {
+		"zod": "^4.4.3"
+	},
+	"peerDependenciesMeta": {
+		"zod": {
+			"optional": true
+		}
 	},
 	"volta": {
 		"extends": "../../package.json"
diff --git a/packages/deploy-helpers/scripts/deps.ts b/packages/deploy-helpers/scripts/deps.ts
index 709957e156..125466ebbd 100644
--- a/packages/deploy-helpers/scripts/deps.ts
+++ b/packages/deploy-helpers/scripts/deps.ts
@@ -8,9 +8,7 @@ export const EXTERNAL_DEPENDENCIES = [
 	// Workspace packages kept external so consumers share a single copy of
 	// types and runtime code (e.g. ParseError instanceof checks).
 	"@cloudflare/cli-shared-helpers",
-	"@cloudflare/containers-shared",
 	"@cloudflare/workers-utils",
-	"@cloudflare/workers-shared",
 	"miniflare",
 
 	// These are externalized to avoid duplication in wrangler's bundle,
@@ -22,4 +20,9 @@ export const EXTERNAL_DEPENDENCIES = [
 	"p-queue",
 	"pretty-bytes",
 	"undici",
+
+	// Externalized so wrangler bundles a single shared zod copy instead of
+	// inlining one via this package. Declared as a peerDependency (the
+	// consumer provides zod).
+	"zod",
 ];
diff --git a/packages/deploy-helpers/src/config.ts b/packages/deploy-helpers/src/config.ts
new file mode 100644
index 0000000000..8af0fec85e
--- /dev/null
+++ b/packages/deploy-helpers/src/config.ts
@@ -0,0 +1,2 @@
+import { ConfigSchema, convertToWranglerConfig } from "@cloudflare/config";
+export { ConfigSchema, convertToWranglerConfig };
diff --git a/packages/deploy-helpers/src/index.ts b/packages/deploy-helpers/src/index.ts
index a550c25e13..ff8a37e85c 100644
--- a/packages/deploy-helpers/src/index.ts
+++ b/packages/deploy-helpers/src/index.ts
@@ -1,4 +1,5 @@
 export * from "./shared/types";
+export { ConfigSchema, convertToWranglerConfig } from "./config";
 export { initDeployHelpersContext } from "./shared/context";
 export { default as deploy } from "./deploy/deploy";
 export type { DeployCallbacks } from "./deploy/deploy";
diff --git a/packages/deploy-helpers/tsup.config.ts b/packages/deploy-helpers/tsup.config.ts
index a6cb0dcb92..f1c8fb887b 100644
--- a/packages/deploy-helpers/tsup.config.ts
+++ b/packages/deploy-helpers/tsup.config.ts
@@ -19,6 +19,11 @@ export default defineConfig(() => [
 		tsconfig: "tsconfig.json",
 		metafile: true,
 		sourcemap: process.env.SOURCEMAPS !== "false",
+		noExternal: [
+			"@cloudflare/config",
+			"@cloudflare/containers-shared",
+			/^@cloudflare\/workers-shared(\/.*)?$/,
+		],
 		external: [
 			/^@cloudflare\//,
 			"blake3-wasm",
@@ -30,6 +35,9 @@ export default defineConfig(() => [
 			"dotenv",
 			"command-exists",
 			"esbuild",
+			// Keep zod external so wrangler (the only consumer) bundles a single
+			// shared copy rather than inlining one here.
+			/^zod(\/.*)?$/,
 		],
 	},
 ]);
diff --git a/packages/wrangler/src/experimental-config/load.ts b/packages/wrangler/src/experimental-config/load.ts
index 5ed655b6d2..a962cf5a35 100644
--- a/packages/wrangler/src/experimental-config/load.ts
+++ b/packages/wrangler/src/experimental-config/load.ts
@@ -1,11 +1,10 @@
 import { existsSync } from "node:fs";
 import path from "node:path";
+import { loadConfig, resolveWorkerDefinition } from "@cloudflare/config";
 import {
 	ConfigSchema,
 	convertToWranglerConfig,
-	loadConfig,
-	resolveWorkerDefinition,
-} from "@cloudflare/config";
+} from "@cloudflare/deploy-helpers";
 import { getCloudflareEnv, UserError } from "@cloudflare/workers-utils";
 import { convertToolingConfig } from "./convert";
 import {
diff --git a/pnpm-lock.yaml b/pnpm-lock.yaml
index 74af328264..60b06a8411 100644
--- a/pnpm-lock.yaml
+++ b/pnpm-lock.yaml
@@ -1852,12 +1852,6 @@ importers:
       '@cloudflare/cli-shared-helpers':
         specifier: workspace:*
         version: link:../cli
-      '@cloudflare/containers-shared':
-        specifier: workspace:*
-        version: link:../containers-shared
-      '@cloudflare/workers-shared':
-        specifier: workspace:*
-        version: link:../workers-shared
       '@cloudflare/workers-utils':
         specifier: workspace:*
         version: link:../workers-utils
@@ -1886,6 +1880,15 @@ importers:
         specifier: catalog:default
         version: 7.24.8
     devDependencies:
+      '@cloudflare/config':
+        specifier: workspace:*
+        version: link:../config
+      '@cloudflare/containers-shared':
+        specifier: workspace:*
+        version: link:../containers-shared
+      '@cloudflare/workers-shared':
+        specifier: workspace:*
+        version: link:../workers-shared
       '@cloudflare/workers-tsconfig':
         specifier: workspace:*
         version: link:../workers-tsconfig
@@ -1925,6 +1928,9 @@ importers:
       vitest:
         specifier: catalog:default
         version: 4.1.0(@opentelemetry/api@1.9.1)(@types/node@22.15.17)(@vitest/ui@4.1.0)(msw@2.12.4(@types/node@22.15.17)(typescript@5.8.3))(vite@8.0.13(@types/node@22.15.17)(esbuild@0.27.3)(jiti@2.6.1)(tsx@4.21.0)(yaml@2.8.1))
+      zod:
+        specifier: ^4.4.3
+        version: 4.4.3
 
   packages/devprod-status-bot:
     devDependencies: