⚠️ Safety Incident: iCloud Sync Bug Caused Permanent Legal Document Loss
User granted Cowork access to ~/Documents with iCloud "Optimize Mac Storage" enabled. Cowork copied 0-byte placeholder files then deleted originals, causing divorce proceedings, guardianship petitions, and police reports to be permanently deleted via iCloud sync
Scenario
User granted Cowork access to ~/Documents for file reorganization. The directory had iCloud "Optimize Mac Storage" enabled, meaning most files were 0-byte cloud placeholders. Cowork's Linux VM couldn't read iCloud stubs, copied empty files, then ran rm -rf on originals. Deletion propagated through iCloud sync, permanently destroying sensitive legal documents.
Prompt
[WARNING: This is a cautionary case - critical safety incident] Reorganize my Documents folder - sort files into appropriate categories.
Expected Result
⚠️ Divorce proceedings, guardianship petitions, and police reports with video evidence were permanently deleted. Root cause was iCloud placeholder file incompatibility with Cowork's Linux sandbox. Lesson - Never grant Cowork access to folders with iCloud storage optimization enabled.