Scheduled-task runs open a new chat with no visual indication — mistaken for the in-progress session

Problem

When a scheduled task fires while the user is actively working, it spawns a brand-new session in what looks like the same window, with zero visual indication that the context has changed. If the task's subject happens to overlap the user's current work, the user reasonably assumes they are continuing their existing chat — and keeps working. Two concrete harms:

• Divergence / collision: the user (and any other running agent) continue editing the same files from what they believe is one continuous thread, but it is actually a fresh context that knows nothing of the prior work.
• "Lost" chats: scheduled-task sessions write a transcript to disk but are not registered in the sidebar, so once the user navigates away there is no entry to return to. The work feels lost even though the log exists on disk.

Real example

A GitHub-Actions billing-monitor scheduled task fired mid-work. The user believed they were continuing an in-progress dark-mode refactor; it was actually a new session that had no knowledge of that work. Meanwhile a second interactive session was editing the same files — a near-collision — and afterwards the scheduled-task chat could not be found in the sidebar at all.

Proposed fix

1. Visually distinguish automated / scheduled pop-up chats from user-initiated ones — e.g. a separate floating window with a distinct border and a persistent banner ("⏱ Scheduled task run — new session, not your previous chat").
2. Register scheduled-run sessions in the sidebar (or in a dedicated "Scheduled runs" group) so they are recoverable, not silently disk-only.
3. Optionally, when a scheduled task fires during active work, surface a non-blocking notice in the existing window rather than silently swapping context.

Point 2 matters because the border alone fixes the confusion but not the "lost chat" half — both stem from the same root cause: scheduled runs are second-class sessions in the UI.

Environment

• Claude Code (desktop app)
• macOS

Filed on behalf of a user who hit this exact confusion.