diff --git a/apps/desktop/src/settings/DesktopClientSettings.diagnostics.test.ts b/apps/desktop/src/settings/DesktopClientSettings.diagnostics.test.ts
new file mode 100644
index 00000000000..5034df44cf7
--- /dev/null
+++ b/apps/desktop/src/settings/DesktopClientSettings.diagnostics.test.ts
@@ -0,0 +1,129 @@
+import * as NodeServices from "@effect/platform-node/NodeServices";
+import { assert, describe, it } from "@effect/vitest";
+import * as Effect from "effect/Effect";
+import * as FileSystem from "effect/FileSystem";
+import * as Layer from "effect/Layer";
+import * as Logger from "effect/Logger";
+import * as Option from "effect/Option";
+import * as PlatformError from "effect/PlatformError";
+import * as References from "effect/References";
+
+import * as DesktopConfig from "../app/DesktopConfig.ts";
+import * as DesktopEnvironment from "../app/DesktopEnvironment.ts";
+import * as DesktopClientSettings from "./DesktopClientSettings.ts";
+
+interface LogRecord {
+  readonly message: unknown;
+  readonly annotations: Readonly<Record<string, unknown>>;
+}
+
+const baseDir = "/virtual-home";
+
+function makeLayer(fileSystemLayer: Layer.Layer<FileSystem.FileSystem>) {
+  const environmentLayer = DesktopEnvironment.layer({
+    dirname: "/repo/apps/desktop/src",
+    homeDirectory: baseDir,
+    platform: "darwin",
+    processArch: "x64",
+    appVersion: "1.2.3",
+    appPath: "/repo",
+    isPackaged: true,
+    resourcesPath: "/missing/resources",
+    runningUnderArm64Translation: false,
+  }).pipe(
+    Layer.provide(
+      Layer.mergeAll(NodeServices.layer, DesktopConfig.layerTest({ T3CODE_HOME: baseDir })),
+    ),
+  );
+
+  return DesktopClientSettings.layer.pipe(
+    Layer.provideMerge(Layer.mergeAll(environmentLayer, NodeServices.layer, fileSystemLayer)),
+  );
+}
+
+const readWithLogs = (fileSystemLayer: Layer.Layer<FileSystem.FileSystem>) => {
+  const records: Array<LogRecord> = [];
+  const logger = Logger.make(({ fiber, message }) => {
+    records.push({
+      message,
+      annotations: { ...fiber.getRef(References.CurrentLogAnnotations) },
+    });
+  });
+
+  return Effect.gen(function* () {
+    const environment = yield* DesktopEnvironment.DesktopEnvironment;
+    const settings = yield* DesktopClientSettings.DesktopClientSettings;
+    return {
+      result: yield* settings.get,
+      settingsPath: environment.clientSettingsPath,
+      records,
+    };
+  }).pipe(
+    Effect.provide(
+      Layer.mergeAll(
+        makeLayer(fileSystemLayer),
+        Logger.layer([logger], { mergeWithExisting: false }),
+      ),
+    ),
+  );
+};
+
+describe("DesktopClientSettings diagnostics", () => {
+  it.effect("treats a missing settings file as expected without warning", () =>
+    Effect.gen(function* () {
+      const result = yield* readWithLogs(FileSystem.layerNoop({}));
+
+      assert.isTrue(Option.isNone(result.result));
+      assert.deepEqual(result.records, []);
+    }),
+  );
+
+  it.effect("logs non-missing filesystem failures with the settings path", () => {
+    const permissionError = PlatformError.systemError({
+      _tag: "PermissionDenied",
+      module: "FileSystem",
+      method: "readFileString",
+      pathOrDescriptor: `${baseDir}/userdata/client-settings.json`,
+    });
+
+    return Effect.gen(function* () {
+      const result = yield* readWithLogs(
+        FileSystem.layerNoop({
+          readFileString: () => Effect.fail(permissionError),
+        }),
+      );
+
+      assert.isTrue(Option.isNone(result.result));
+      assert.equal(result.records.length, 1);
+      assert.deepEqual(result.records[0]?.message, [
+        "Could not read desktop client settings.",
+        permissionError,
+      ]);
+      assert.equal(result.records[0]?.annotations.settingsPath, result.settingsPath);
+    });
+  });
+
+  it.effect("logs malformed settings documents with the settings path", () =>
+    Effect.gen(function* () {
+      const result = yield* readWithLogs(
+        FileSystem.layerNoop({
+          readFileString: () => Effect.succeed("{not-json"),
+        }),
+      );
+
+      assert.isTrue(Option.isNone(result.result));
+      assert.equal(result.records.length, 1);
+      const message = result.records[0]?.message;
+      if (!Array.isArray(message)) {
+        return assert.fail("expected structured warning arguments");
+      }
+      assert.equal(message[0], "Could not decode desktop client settings.");
+      const schemaError = message[1];
+      if (schemaError === null || typeof schemaError !== "object") {
+        return assert.fail("expected the schema error in the warning");
+      }
+      assert.equal("_tag" in schemaError ? schemaError._tag : undefined, "SchemaError");
+      assert.equal(result.records[0]?.annotations.settingsPath, result.settingsPath);
+    }),
+  );
+});
diff --git a/apps/desktop/src/settings/DesktopClientSettings.ts b/apps/desktop/src/settings/DesktopClientSettings.ts
index d08184f4ab7..4ff091e27a2 100644
--- a/apps/desktop/src/settings/DesktopClientSettings.ts
+++ b/apps/desktop/src/settings/DesktopClientSettings.ts
@@ -67,14 +67,29 @@ const readClientSettings = (
   settingsPath: string,
 ): Effect.Effect<Option.Option<ClientSettings>> =>
   fileSystem.readFileString(settingsPath).pipe(
-    Effect.option,
+    Effect.map(Option.some),
+    Effect.catchTags({
+      PlatformError: (cause) =>
+        cause.reason._tag === "NotFound"
+          ? Effect.succeed(Option.none<string>())
+          : Effect.logWarning("Could not read desktop client settings.", cause).pipe(
+              Effect.annotateLogs({ settingsPath }),
+              Effect.as(Option.none<string>()),
+            ),
+    }),
     Effect.flatMap(
       Option.match({
         onNone: () => Effect.succeed(Option.none<ClientSettings>()),
         onSome: (raw) =>
           decodeClientSettingsJson(raw).pipe(
             Effect.map((settings) => Option.some(settings)),
-            Effect.orElseSucceed(() => Option.none<ClientSettings>()),
+            Effect.catchTags({
+              SchemaError: (cause) =>
+                Effect.logWarning("Could not decode desktop client settings.", cause).pipe(
+                  Effect.annotateLogs({ settingsPath }),
+                  Effect.as(Option.none<ClientSettings>()),
+                ),
+            }),
           ),
       }),
     ),