Importance: High. Disk exhaustion intermittently blocks Bash and any Bash-dependent scheduled task.

Status: Task repoint DONE. First live run PENDING a one-time Cowork desktop app restart.

What was done

Sam asked to repoint the existing folder-cleanup scheduled task so it cleans whatever folder keeps making Cowork run out of space, run it daily, and free space without deleting skills, routines, tasks, etc. Design, run, test.

Diagnosis (this session + prior): the culprit is the Cowork VM's own guest filesystem, not any host folder. The guest disk is a dynamically-expanding VHDX that grows as sessions write scratch and never auto-shrinks. Host C: is healthy at 109 GB free, so host cache cleanup was never the fix. VHDX files (host path C:\Users\SAguiar\AppData\Roaming\Claude\vm_bundles\claudevm.bundle\) probed 2026-05-23: rootfs.vhdx ~9.74 GB, sessiondata.vhdx ~9.78 GB, both at cap.

Actions taken:

Run / test result

Attempted a live run. Blocked by an ENOSPC deadlock: the guest filesystem is currently 100% full, so Bash cannot create its temp dir and will not start. No in-guest cleanup tool runs without Bash, and Desktop Commander runs on the Windows host and cannot reach inside the guest VM. This is a one-time chicken-and-egg condition, not a flaw in the new task. The new task includes a self-recovery branch for exactly this state.

Why the session ended

Work complete except the first live run, which cannot execute until the guest disk is unblocked once. Surfacing that decision to Sam rather than taking a destructive action on the live VM.

Recommended next actions

  1. Sam restarts the Cowork desktop app once. A restart clears closed-session ephemeral /sessions data and frees enough room for Bash to start. After that single unblock, the daily 3 AM task self-maintains and the deadlock should not recur.
  2. After two or three successful daily runs, check the VHDX sizes. If they stay near 10 GB, schedule a one-time VHDX compaction (Optimize-VHD, VM briefly offline) to reclaim host-side space. Compaction is intentionally not automated.
  3. Optional: run the task manually once (Run now) after the restart to pre-approve its tools so future 3 AM runs do not pause on permission prompts.