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Desktop: sessions spawned by scheduled tasks missing from Recents and unpinnable (Search-only); Routines sidebar section intermittent #78229

Description

@Milesenberg

Environment

What happens

  1. Sessions created by scheduled tasks (both cron and one-time fireAt) never appear in the Recents sidebar list — including sessions the user has already opened and exchanged messages with from the mobile app. Interacting with a spawned session does not surface it either.
  2. These sessions cannot be pinned — no working pin affordance is offered for them.
  3. They ARE returned by Search, and the session-management MCP (list_sessions) returns them with correct metadata — the sessions exist and are healthy server-side. This looks like a sidebar/session-index gap, not data loss.
  4. Related wobble: the "Routines" collapsible sidebar section (shown parallel to Pinned/Recents) appears on some launches and is absent on others — e.g., present before a relaunch-to-update, gone immediately after it, on the same day.

Impact

With a daily scheduled fleet, effectively none of the user's working sessions are visible in the sidebar. Every navigation goes through Search by remembered title, and pinning — the natural workaround — is unavailable for exactly the affected sessions. The dedicated Routines page lists the tasks, not the sessions they spawn, so it doesn't substitute.

Repro

  1. Create a scheduled task (cron or one-time fireAt) whose prompt runs a normal interactive session.
  2. Let it fire; confirm the spawned session exists via Search or the session-management list_sessions.
  3. Interact with that session (e.g., reply from the mobile app).
  4. Check the desktop sidebar: absent from Recents; pin unavailable; Search finds it.

Expected

Recents should be all sessions ordered by last activity, including task-spawned ones. At minimum, any scheduled session the user has interacted with should appear in Recents exactly like a hand-started session. Ideally, scheduled runs with no user interaction yet would be collapsible/filterable within Recents so nightly fleets don't flood the list.

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    area:desktoparea:routinesClaude Code routines on web, used for scheduled tasks, webhook-triggered tasks, etc.area:uibugSomething isn't workingplatform:windowsIssue specifically occurs on Windows

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