[FEATURE] Allow custom or AI-generated conversation session titles

Preflight Checklist

• [x] I have searched existing requests and this feature hasn't been requested yet
• [x] This is a single feature request (not multiple features)

Problem Statement

When using claude --resume to browse past sessions, the titles are hard to scan — they show the last message content, which is often generic or truncated.

Proposed Solution

1. Option to set a custom title for a session (e.g., /title "agent bot 2nd API layer fixes")
2. Or option to have AI generate a meaningful title based on the conversation content
3. A config option like session_title_mode: auto | manual | ai in settings

Why this matters:

When working on a complex project across many sessions, claude --resume lists dozens of sessions with titles like "can u give me this bot .." or "deploy and set secrets" — these don't tell you what the session
actually accomplished. A descriptive title like "Agent bot: event-driven exits + sell verification" would make it much easier to find and resume the right session.

Alternative Solutions

_No response_

Priority

High - Significant impact on productivity

Feature Category

CLI commands and flags

Use Case Example

_No response_

Additional Context

_No response_