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May 26, 2026

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.

Also today

  • Simon Willison
  • Teresa Torres
  • Lenny Rachitsky
  • Cursor
  • AWS
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