When AI Makes Mistakes in Your Files: Copilot's Trust Problem
AI PM Research
Tuesday, May 26, 2026
When AI Makes Mistakes in Your Files: Copilot's Trust Problem
Simon Willison flagged a real security issue in Microsoft Copilot Cowork — file exfiltration via prompt injection — and it lands right as ElevenLabs ships Music v2. Two very different stories about what "AI in production" actually looks like right now: one about the failure modes that erode trust, one about a product category quietly maturing.
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- Simon Willison
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