[jlongo78]

The search feature would be huge - that friction of "which session was working on X" is exactly where things break down.

On the context side, maybe a short freeform note field attached at session creation? Branch name gets you partway there but doesn't capture intent. Something like "refactoring auth layer - blocked on X" would make resurrection much faster after a few days away.

I work mostly in backend infra and developer tooling.

[raykamp]

OK, that's great input.

Expanding on that idea, the short freeform note/summary could be optionally auto generated and continually maintained (if scope shifts) by the Claude session. Akin to AI summarizing changes and writing git commits for us.

[jlongo78]

That auto-generated summary idea is sharp. The session basically narrates its own purpose as it evolves, so you never have to reconstruct context after stepping away. Similar to how good commit messages document intent, not just changes. The tricky part is keeping summaries tight when scope creeps - you'd want the model to flag drift rather than just silently updating, so you actually notice when a session has become two problems pretending to be one.