fix(server): retry automatic thread title generation

apps/server/src/orchestration/Layers/ProviderCommandReactor.test.ts

@@ -728,6 +728,62 @@ describe("ProviderCommandReactor", () => {
     expect(thread?.title).toBe("Generated title");
   });
 
+  effectIt.effect("retries thread title generation after a transient failure", () =>
+    Effect.gen(function* () {
+      const harness = yield* Effect.promise(() => createHarness());
+      const now = "2026-01-01T00:00:00.000Z";
+      const seededTitle = "Please investigate reconnect failures after restar...";
+      let attempts = 0;
+      harness.generateThreadTitle.mockReturnValue(
+        Effect.suspend(() => {
+          attempts += 1;
+          return attempts === 1
+            ? Effect.fail(
+                new TextGenerationError({
+                  operation: "generateThreadTitle",
+                  detail: "Claude CLI request timed out.",
+                }),
+              )
+            : Effect.succeed({ title: "Generated title" });
+        }),
+      );
+
+      yield* harness.engine.dispatch({
+        type: "thread.meta.update",
+        commandId: CommandId.make("cmd-thread-title-retry-seed"),
+        threadId: ThreadId.make("thread-1"),
+        title: seededTitle,
+      });
+
+      yield* harness.engine.dispatch({
+        type: "thread.turn.start",
+        commandId: CommandId.make("cmd-turn-start-title-retry"),
+        threadId: ThreadId.make("thread-1"),
+        message: {
+          messageId: asMessageId("user-message-title-retry"),
+          role: "user",
+          text: "Please investigate reconnect failures after restarting the session.",
+          attachments: [],
+        },
+        titleSeed: seededTitle,
+        interactionMode: DEFAULT_PROVIDER_INTERACTION_MODE,
+        runtimeMode: "approval-required",
+        createdAt: now,
+      });
+
+      yield* Effect.promise(() =>
+        waitFor(async () => {
+          const readModel = await harness.readModel();
+          return (
+            readModel.threads.find((entry) => entry.id === ThreadId.make("thread-1"))?.title ===
+            "Generated title"
+          );
+        }),
+      );
+      expect(attempts).toBe(2);
+    }),
+  );
+
   it("regenerates a thread title from the current conversation", async () => {
     const harness = await createHarness();
     const now = "2026-01-01T00:00:00.000Z";

apps/server/src/orchestration/Layers/ProviderCommandReactor.ts

@@ -22,6 +22,7 @@ import * as Equal from "effect/Equal";
 import * as FileSystem from "effect/FileSystem";
 import * as Layer from "effect/Layer";
 import * as Option from "effect/Option";
+import * as Schedule from "effect/Schedule";
 import * as Schema from "effect/Schema";
 import * as Stream from "effect/Stream";
 import { makeDrainableWorker } from "@t3tools/shared/DrainableWorker";
@@ -94,6 +95,12 @@ const HANDLED_TURN_START_KEY_MAX = 10_000;
 const HANDLED_TURN_START_KEY_TTL = Duration.minutes(30);
 const DEFAULT_RUNTIME_MODE: RuntimeMode = "full-access";
 const MAX_REGENERATION_ATTACHMENTS = 4;
+// Automatic title generation is fire-and-forget: when it fails the thread keeps
+// the placeholder title the client seeded from the first message, and nothing
+// ever tries again. Retry so a transient CLI timeout or auth failure does not
+// permanently leave the thread named after the raw prompt text.
+const THREAD_TITLE_GENERATION_RETRIES = 2;
+const THREAD_TITLE_RETRY_DELAY = Duration.seconds(2);
 const MAX_THREAD_TITLE_CONTEXT_CHARS = 8_000;
 const MAX_FIRST_USER_TITLE_CONTEXT_CHARS = 2_000;
 const THREAD_TITLE_CONTEXT_TRUNCATION_MARKER = "[Earlier content truncated]\n\n";
@@ -905,12 +912,19 @@ const make = Effect.gen(function* () {
         const { textGenerationModelSelection: modelSelection } =
           yield* serverSettingsService.getSettings;
 
-        const generated = yield* textGeneration.generateThreadTitle({
-          cwd: input.cwd,
-          message: input.messageText,
-          ...(attachments.length > 0 ? { attachments } : {}),
-          modelSelection,
-        });
+        const generated = yield* textGeneration
+          .generateThreadTitle({
+            cwd: input.cwd,
+            message: input.messageText,
+            ...(attachments.length > 0 ? { attachments } : {}),
+            modelSelection,
+          })
+          .pipe(
+            Effect.retry({
+              times: THREAD_TITLE_GENERATION_RETRIES,
+              schedule: Schedule.exponential(THREAD_TITLE_RETRY_DELAY),
+            }),
+          );
         if (!generated) return;
 
         const thread = yield* resolveThread(input.threadId);