Bug/UX] ChatGPT loses access to previously uploaded project files – no way to reconnect

[engsilas]

🧠 Context

When working with project files in ChatGPT, users can upload .zip or other files to the "uploads" panel in a project and expect them to be reusable throughout the session. However, the model loses access to these files across executions – even in the same conversation, and even after confirming the file's presence earlier.

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❌ Problem

The file appears in the sidebar and was already accessed and confirmed by the model (e.g. the model lists files or shows contents). Later, if the user asks:

"Please re-extract the .zip file I uploaded earlier"

The model responds:

"That file is not in the zip"

This is despite having previously confirmed it was.

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🔍 Root cause (likely)

It seems the execution environment (sandbox) is ephemeral. When the environment resets, the model can no longer access previously extracted content or uploaded files – even though the project interface shows them.

There is no way for the user to reconnect a file to the model, and the model does not notify the user that access to the file was lost.

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🧭 Expected behavior

• Files uploaded to a project should be accessible across executions.
• The model should be able to reference them reliably via filename or ID.
• At minimum, the user should be able to click "Reconnect this file to model" in the UI.
• If the model cannot access a previously seen file, it should say:

  "I’ve lost access to the file – please reupload it."

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✅ Recommendation

• Add persistent access to project uploads
• Provide a UI way to “reconnect” a file
• Improve model feedback when a file is no longer accessible