Vendors and modelsModelby Anthropic

Claude Cowork AI failures

Every documented AI failure involving Claude Cowork on the AI Failure Index, classified by the mechanism that broke.

Failures
1
Highest severity
High
Span
2026
Failure modes
1
By failure mode
By severity
FI-0032Cross-industryHigh
Agentic Action Error

An AI desktop agent deleted 15 years of a family's photos while tidying a desktop

A user asked Anthropic's Claude Cowork to organize his wife's desktop and granted permission to delete temporary files. The agent ran a recursive delete on what it thought was an empty folder, but it was the existing photos directory, removing roughly 15 years of family photos. The files were recovered only via cloud retention.

Confidence
Medium (multi-source)
Anthropic (Claude Cowork)2 sourcesPressPublicFeb 2026

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