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VC Says Anthropic’s Claude Agent Deleted 15 Years of Family Photos

Apple’s 30-day iCloud Drive restore is bringing back the images.

Overview

  • Nick Davidov reported that Anthropic’s desktop agent, Claude Cowork, deleted a folder of long-term family photographs after he granted permission to remove temporary Office files.
  • The removal occurred via terminal commands, so nothing appeared in Trash, iCloud had already synced the new structure, and no Time Machine backup was available.
  • Apple support directed Davidov to iCloud Drive’s feature that retains deleted files for 30 days, enabling the restoration of tens of thousands of items.
  • Claude Cowork, described in reporting as a general-purpose desktop agent with broad file access, can read, create, and manipulate local files, including executing system-level operations.
  • Davidov cautioned others against granting such tools deep access to local file systems, and the episode fueled online discussion about safety, consent, and mainstream readiness for desktop AI agents.