diff --git a/.sisyphus/notepads/rebase-v146/decisions.md b/.sisyphus/notepads/rebase-v146/decisions.md
new file mode 100644
index 000000000000..9640c721faa6
--- /dev/null
+++ b/.sisyphus/notepads/rebase-v146/decisions.md
@@ -0,0 +1,3 @@
+- Rebuilt `packages/opencode/src/session/prompt.ts` and `packages/opencode/test/session/prompt-effect.test.ts` from clean `dev`, then replayed only the branch's surviving behavioral deltas.
+- Preserved three prompt behaviors only: previous user agent fallback in `createUserMessage`, re-read guard before loop exit, and simple `return yield* loop(...)` in `prompt()`.
+- Kept upstream abort-propagation coverage and re-added the branch's `cancel does not restart session via prompt retry loop` regression test.
diff --git a/.sisyphus/notepads/rebase-v146/issues.md b/.sisyphus/notepads/rebase-v146/issues.md
new file mode 100644
index 000000000000..9ec878e4346f
--- /dev/null
+++ b/.sisyphus/notepads/rebase-v146/issues.md
@@ -0,0 +1,2 @@
+- `bun typecheck` initially failed because workspace dependencies were not installed in this jj workspace (`tsgo` missing from PATH). Running `bun install` at repo root restored the expected toolchain and `bun typecheck` then passed.
+- `lsp_diagnostics` still reports TypeScript errors on `prompt.ts`, `prompt-effect.test.ts`, and the two branch regression tests even after `bun typecheck` passes; this appears to be a tsserver/LSP mismatch against the repo's `tsgo`-based typecheck path rather than a blocking `tsgo` error.
diff --git a/packages/opencode/src/session/processor.ts b/packages/opencode/src/session/processor.ts
index b02e7cc81cd3..e3435a031126 100644
--- a/packages/opencode/src/session/processor.ts
+++ b/packages/opencode/src/session/processor.ts
@@ -560,6 +560,11 @@ export namespace SessionProcessor {
                   }
                 }),
               ),
+              // Safety timeout: if the stream hangs (stuck tool, lost context),
+              // interrupt after 30 minutes rather than blocking the session forever.
+              // The interrupt triggers onInterrupt above which calls halt().
+              Effect.timeout("30 minutes"),
+              Effect.asVoid,
               Effect.catchCauseIf(
                 (cause) => !Cause.hasInterruptsOnly(cause),
                 (cause) => Effect.fail(Cause.squash(cause)),
diff --git a/packages/opencode/src/session/prompt.ts b/packages/opencode/src/session/prompt.ts
index ffd074d3f8b4..81b8a93d8f74 100644
--- a/packages/opencode/src/session/prompt.ts
+++ b/packages/opencode/src/session/prompt.ts
@@ -923,7 +923,10 @@ NOTE: At any point in time through this workflow you should feel free to ask the
       })
 
       const createUserMessage = Effect.fn("SessionPrompt.createUserMessage")(function* (input: PromptInput) {
-        const agentName = input.agent || (yield* agents.defaultAgent())
+        const prev = (yield* MessageV2.filterCompactedEffect(input.sessionID)).findLast(
+          (m) => m.info.role === "user" && !!m.info.agent,
+        )
+        const agentName = input.agent || prev?.info.agent || (yield* agents.defaultAgent())
         const ag = yield* agents.get(agentName)
         if (!ag) {
           const available = (yield* agents.list()).filter((a) => !a.hidden).map((a) => a.name)
@@ -1355,6 +1358,12 @@ NOTE: At any point in time through this workflow you should feel free to ask the
               !hasToolCalls &&
               lastUser.id < lastAssistant.id
             ) {
+              const fresh = yield* MessageV2.filterCompactedEffect(sessionID)
+              const newest = fresh.findLast((m) => m.info.role === "user")
+              if (newest && newest.info.id > lastAssistant.id) {
+                yield* slog.info("continuing loop for new user")
+                continue
+              }
               yield* slog.info("exiting loop")
               break
             }
diff --git a/packages/opencode/test/session/prompt-agent-preserve.test.ts b/packages/opencode/test/session/prompt-agent-preserve.test.ts
new file mode 100644
index 000000000000..676728e3ea9e
--- /dev/null
+++ b/packages/opencode/test/session/prompt-agent-preserve.test.ts
@@ -0,0 +1,134 @@
+import { afterEach, expect, test } from "bun:test"
+import { Effect, Layer } from "effect"
+import { Instance } from "../../src/project/instance"
+import { ModelID, ProviderID } from "../../src/provider/schema"
+import { Session } from "../../src/session"
+import { MessageV2 } from "../../src/session/message-v2"
+import { SessionPrompt } from "../../src/session/prompt"
+import { MessageID, PartID } from "../../src/session/schema"
+import { Log } from "../../src/util/log"
+import { tmpdir } from "../fixture/fixture"
+
+Log.init({ print: false })
+
+afterEach(async () => {
+  await Instance.disposeAll()
+})
+
+const ref = {
+  providerID: ProviderID.make("test"),
+  modelID: ModelID.make("test-model"),
+}
+
+async function withoutWatcher<T>(fn: () => Promise<T>) {
+  if (process.platform !== "win32") return fn()
+  const prev = process.env.OPENCODE_EXPERIMENTAL_DISABLE_FILEWATCHER
+  process.env.OPENCODE_EXPERIMENTAL_DISABLE_FILEWATCHER = "true"
+  try {
+    return await fn()
+  } finally {
+    if (prev === undefined) delete process.env.OPENCODE_EXPERIMENTAL_DISABLE_FILEWATCHER
+    else process.env.OPENCODE_EXPERIMENTAL_DISABLE_FILEWATCHER = prev
+  }
+}
+
+test("prompt without agent field preserves session's current agent", async () => {
+  await using tmp = await tmpdir({
+    git: true,
+    config: {
+      provider: {
+        test: {
+          name: "Test",
+          id: "test",
+          env: [],
+          npm: "@ai-sdk/openai-compatible",
+          models: {
+            "test-model": {
+              id: "test-model",
+              name: "Test Model",
+              attachment: false,
+              reasoning: false,
+              temperature: false,
+              tool_call: true,
+              release_date: "2025-01-01",
+              limit: { context: 100000, output: 10000 },
+              cost: { input: 0, output: 0 },
+              options: {},
+            },
+          },
+          options: {
+            apiKey: "test-key",
+            baseURL: "http://localhost:1/v1",
+          },
+        },
+      },
+    },
+  })
+  await withoutWatcher(() =>
+    Instance.provide({
+      directory: tmp.path,
+      fn: () =>
+        Effect.runPromise(
+          Effect.gen(function* () {
+            const prompt = yield* SessionPrompt.Service
+            const sessions = yield* Session.Service
+            const session = yield* sessions.create({
+              permission: [{ permission: "*", pattern: "*", action: "allow" }],
+            })
+
+            const uid = MessageID.ascending()
+            yield* sessions.updateMessage({
+              id: uid,
+              sessionID: session.id,
+              role: "user",
+              agent: "plan",
+              model: ref,
+              time: { created: Date.now() },
+            } satisfies MessageV2.User)
+            yield* sessions.updatePart({
+              id: PartID.ascending(),
+              sessionID: session.id,
+              messageID: uid,
+              type: "text",
+              text: "make a plan",
+            } satisfies MessageV2.TextPart)
+
+            const aid = MessageID.ascending()
+            yield* sessions.updateMessage({
+              id: aid,
+              sessionID: session.id,
+              role: "assistant",
+              parentID: uid,
+              agent: "plan",
+              mode: "plan",
+              cost: 0,
+              path: { cwd: "/tmp", root: "/tmp" },
+              tokens: { input: 0, output: 0, reasoning: 0, cache: { read: 0, write: 0 } },
+              modelID: ref.modelID,
+              providerID: ref.providerID,
+              time: { created: Date.now() },
+              finish: "stop",
+            } satisfies MessageV2.Assistant)
+            yield* sessions.updatePart({
+              id: PartID.ascending(),
+              sessionID: session.id,
+              messageID: aid,
+              type: "text",
+              text: "here is the plan",
+            } satisfies MessageV2.TextPart)
+
+            const msg = yield* prompt.prompt({
+              sessionID: session.id,
+              noReply: true,
+              parts: [{ type: "text", text: "notification: task completed" }],
+            })
+
+            expect(msg.info.role).toBe("user")
+            if (msg.info.role === "user") {
+              expect(msg.info.agent).toBe("plan")
+            }
+          }).pipe(Effect.scoped, Effect.provide(Layer.mergeAll(SessionPrompt.defaultLayer, Session.defaultLayer))),
+        ),
+    }),
+  )
+}, 15000)
diff --git a/packages/opencode/test/session/prompt-async-orphan.test.ts b/packages/opencode/test/session/prompt-async-orphan.test.ts
new file mode 100644
index 000000000000..2b03e0c9e705
--- /dev/null
+++ b/packages/opencode/test/session/prompt-async-orphan.test.ts
@@ -0,0 +1,149 @@
+import { afterEach, expect, test } from "bun:test"
+import { Effect, Layer } from "effect"
+import { Instance } from "../../src/project/instance"
+import { ModelID, ProviderID } from "../../src/provider/schema"
+import { Session } from "../../src/session"
+import { MessageV2 } from "../../src/session/message-v2"
+import { SessionPrompt } from "../../src/session/prompt"
+import { MessageID, PartID } from "../../src/session/schema"
+import { Log } from "../../src/util/log"
+import { tmpdir } from "../fixture/fixture"
+
+Log.init({ print: false })
+
+afterEach(async () => {
+  await Instance.disposeAll()
+})
+
+const ref = {
+  providerID: ProviderID.make("test"),
+  modelID: ModelID.make("test-model"),
+}
+
+async function withoutWatcher<T>(fn: () => Promise<T>) {
+  if (process.platform !== "win32") return fn()
+  const prev = process.env.OPENCODE_EXPERIMENTAL_DISABLE_FILEWATCHER
+  process.env.OPENCODE_EXPERIMENTAL_DISABLE_FILEWATCHER = "true"
+  try {
+    return await fn()
+  } finally {
+    if (prev === undefined) delete process.env.OPENCODE_EXPERIMENTAL_DISABLE_FILEWATCHER
+    else process.env.OPENCODE_EXPERIMENTAL_DISABLE_FILEWATCHER = prev
+  }
+}
+
+test("prompt_async to busy session does not orphan user message", async () => {
+  await using tmp = await tmpdir({
+    git: true,
+    config: {
+      provider: {
+        test: {
+          name: "Test",
+          id: "test",
+          env: [],
+          npm: "@ai-sdk/openai-compatible",
+          models: {
+            "test-model": {
+              id: "test-model",
+              name: "Test Model",
+              attachment: false,
+              reasoning: false,
+              temperature: false,
+              tool_call: true,
+              release_date: "2025-01-01",
+              limit: { context: 100000, output: 10000 },
+              cost: { input: 0, output: 0 },
+              options: {},
+            },
+          },
+          options: {
+            apiKey: "test-key",
+            baseURL: "http://localhost:1/v1",
+          },
+        },
+      },
+    },
+  })
+  await withoutWatcher(() =>
+    Instance.provide({
+      directory: tmp.path,
+      fn: () =>
+        Effect.runPromise(
+          Effect.gen(function* () {
+            const prompt = yield* SessionPrompt.Service
+            const sessions = yield* Session.Service
+            const session = yield* sessions.create({
+              permission: [{ permission: "*", pattern: "*", action: "allow" }],
+            })
+
+            const uid1 = MessageID.ascending()
+            yield* sessions.updateMessage({
+              id: uid1,
+              sessionID: session.id,
+              role: "user",
+              agent: "build",
+              model: ref,
+              time: { created: Date.now() },
+            } satisfies MessageV2.User)
+            yield* sessions.updatePart({
+              id: PartID.ascending(),
+              sessionID: session.id,
+              messageID: uid1,
+              type: "text",
+              text: "first question",
+            } satisfies MessageV2.TextPart)
+
+            const aid = MessageID.ascending()
+            yield* sessions.updateMessage({
+              id: aid,
+              sessionID: session.id,
+              role: "assistant",
+              parentID: uid1,
+              agent: "build",
+              mode: "build",
+              cost: 0,
+              path: { cwd: "/tmp", root: "/tmp" },
+              tokens: { input: 0, output: 0, reasoning: 0, cache: { read: 0, write: 0 } },
+              modelID: ref.modelID,
+              providerID: ref.providerID,
+              time: { created: Date.now() },
+              finish: "stop",
+            } satisfies MessageV2.Assistant)
+            yield* sessions.updatePart({
+              id: PartID.ascending(),
+              sessionID: session.id,
+              messageID: aid,
+              type: "text",
+              text: "first answer",
+            } satisfies MessageV2.TextPart)
+
+            const uid2 = MessageID.ascending()
+            yield* sessions.updateMessage({
+              id: uid2,
+              sessionID: session.id,
+              role: "user",
+              agent: "build",
+              model: ref,
+              time: { created: Date.now() },
+            } satisfies MessageV2.User)
+            yield* sessions.updatePart({
+              id: PartID.ascending(),
+              sessionID: session.id,
+              messageID: uid2,
+              type: "text",
+              text: "second question (from prompt_async)",
+            } satisfies MessageV2.TextPart)
+
+            const result = yield* Effect.promise(() =>
+              Promise.race([
+                Effect.runPromise(prompt.loop({ sessionID: session.id })).then(() => "exited" as const),
+                new Promise<"continued">((r) => setTimeout(() => r("continued"), 3000)),
+              ]),
+            )
+
+            expect(result).toBe("continued")
+          }).pipe(Effect.scoped, Effect.provide(Layer.mergeAll(SessionPrompt.defaultLayer, Session.defaultLayer))),
+        ),
+    }),
+  )
+}, 15000)
diff --git a/packages/opencode/test/session/prompt-effect.test.ts b/packages/opencode/test/session/prompt-effect.test.ts
index 94561206e2ef..8be28b4626f8 100644
--- a/packages/opencode/test/session/prompt-effect.test.ts
+++ b/packages/opencode/test/session/prompt-effect.test.ts
@@ -747,6 +747,43 @@ it.live(
   3_000,
 )
 
+it.live(
+  "cancel does not restart session via prompt retry loop",
+  () =>
+    provideTmpdirServer(
+      Effect.fnUntraced(function* ({ llm }) {
+        const prompt = yield* SessionPrompt.Service
+        const sessions = yield* Session.Service
+        const chat = yield* sessions.create({
+          title: "CancelNoRestart",
+          permission: [{ permission: "*", pattern: "*", action: "allow" }],
+        })
+
+        yield* llm.hang
+
+        const fiber = yield* prompt
+          .prompt({
+            sessionID: chat.id,
+            agent: "build",
+            parts: [{ type: "text", text: "hello" }],
+          })
+          .pipe(Effect.forkChild)
+
+        yield* llm.wait(1)
+        expect(yield* llm.calls).toBe(1)
+
+        yield* prompt.cancel(chat.id)
+        const exit = yield* Fiber.await(fiber)
+        expect(Exit.isSuccess(exit)).toBe(true)
+
+        yield* Effect.sleep("200 millis")
+        expect(yield* llm.calls).toBe(1)
+      }),
+      { git: true, config: providerCfg },
+    ),
+  5_000,
+)
+
 it.live(
   "cancel records MessageAbortedError on interrupted process",
   () =>