Session title stays 'Untitled session' even after extended conversation

Description

A session in Claude Code (desktop/IDE UI) remained titled "Untitled session" in the sidebar even after a long, multi-turn conversation that included several tool calls, file edits, git commits, and a PR creation via the /create-pr command.

Normally the app auto-generates a session title from the conversation shortly after it starts, but that did not happen in this case.

Steps to reproduce

1. Start a new session.
2. Immediately invoke a slash command (e.g. /create-pr) or otherwise proceed through several tool-driven steps without an initial free-text prompt.
3. Continue the conversation for multiple turns (file edits, commits, PR creation, etc.).
4. Observe that the session in the sidebar is still labeled "Untitled session" instead of an auto-generated title reflecting the conversation content.

Expected behavior

The session should be auto-titled based on the conversation content within the first few turns, regardless of whether the first interaction was a slash command.

Actual behavior

Session remains "Untitled session" indefinitely (see attached screenshot from the reporting session).

Environment

• Claude Code desktop/IDE UI
• Session included: file edits, git commit, git push, gh pr create (PR https://github.com/radi-digital/jenga/pull/566)

Additional notes

Suspected cause: title auto-generation may be gated on the first message being free-text rather than a slash command, so sessions that start with a command (or where the harness enters mid-flow) never trigger the naming logic.

Screenshot

See, our title remains "Untitled session"

<img width="1927" height="997" alt="Image" src="https://github.com/user-attachments/assets/de6a92d8-05cf-4ebd-9f0b-062a910e3a33" />