Feature: Auto-evolving session titles that update as conversation progresses

Problem

Currently, Claude Code auto-generates a session title at the start of a conversation, but it remains static. As conversations evolve — covering multiple topics, shifting focus, or diving deeper into specifics — the initial title becomes stale and no longer reflects the actual content.

When switching between multiple sessions, users have to scroll through old messages to remember what each session was about. The /rename command exists but requires manual effort every time the conversation shifts.

Proposed Solution

Auto-update the session title as the conversation progresses, similar to how the initial title is generated but triggered periodically when the topic shifts significantly. For example:

1. Initial message: "How do I set up auth?" → Title: "Auth setup"
2. Conversation evolves into JWT vs session debate → Title updates to: "Auth: JWT vs sessions comparison"
3. User starts implementing → Title updates to: "Implementing JWT auth middleware"

Suggested behavior

• Title updates should be infrequent (not every message) — only when the conversation focus meaningfully shifts
• The update should happen in the background without interrupting the user
• Users should be able to disable this via settings if they prefer static titles
• Previous auto-generated titles could be kept in history for searchability

Why this matters

• Power users run many parallel sessions (e.g., one for debugging, one for feature work, one for research)
• Descriptive, up-to-date titles are essential for fast context-switching
• Manual /rename adds friction and breaks flow

Environment

• VS Code extension
• macOS