diff --git a/docs/refactor/2025-11-26-auto-reply-split.md b/docs/refactor/2025-11-26-auto-reply-split.md
index b329d4fbe..9d10af786 100644
--- a/docs/refactor/2025-11-26-auto-reply-split.md
+++ b/docs/refactor/2025-11-26-auto-reply-split.md
@@ -5,6 +5,7 @@
   - Audio transcription helpers live in `src/auto-reply/transcription.ts`.
   - Shared reply types live in `src/auto-reply/types.ts` (re-exported from `reply.ts`).
 - `runCommandReply` now returns `{ payload, meta }`, supports injected enqueue runners for tests, logs structured metadata, and respects `mediaMaxMb` for local media paths.
+- Timeout messaging now includes `cwd` when provided to speed up debugging slow commands.
 - Added focused tests:
   - `src/auto-reply/command-reply.test.ts` exercises Claude flag injection, session args, timeout messaging, media token handling, and Claude metadata reporting.
   - `src/auto-reply/transcription.test.ts` covers media download + transcription command invocation.
diff --git a/src/auto-reply/command-reply.ts b/src/auto-reply/command-reply.ts
index af8b00c17..75ede80db 100644
--- a/src/auto-reply/command-reply.ts
+++ b/src/auto-reply/command-reply.ts
@@ -341,7 +341,7 @@ export async function runCommandReply(
       );
       const baseMsg =
         "Command timed out after " +
-        `${timeoutSeconds}s. Try a shorter prompt or split the request.`;
+        `${timeoutSeconds}s${reply.cwd ? ` (cwd: ${reply.cwd})` : ""}. Try a shorter prompt or split the request.`;
       const partial = errorObj.stdout?.trim();
       const partialSnippet =
         partial && partial.length > 800 ? `${partial.slice(0, 800)}...` : partial;