The Information Machine

Quoting OpenAI

Simon Willison · Simon Willison · 2026-07-10

Simon Willison calls out OpenAI's confusing explanation of ChatGPT Work's cloud-versus-desktop data separation, where cloud conversations do not sync to the desktop app at launch.

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Topics: chatgpt-workopenaiproduct-ux

Claims

  • ChatGPT Work on web and mobile runs in the cloud, while the desktop app can additionally access local files.
  • At launch, cloud Work conversations do not appear in the desktop Work interface, creating a fragmented experience.
  • OpenAI's own quoted explanation of this behavior is unclear and does not resolve the confusion.

Key quotes

Work on web and mobile runs in the cloud. Work in the desktop app can also use local files and desktop apps with your permission. At launch, cloud Work conversations do not appear in desktop Work; desktop Work threads and local files remain on that computer.