ChatGPT saves the files you upload to Library on its own: "ChatGPT automatically saves uploaded and created files, including files uploaded in chats". Deleting the chat doesn't remove them. OpenAI's help pages (read 27 Oct 2026): "Deleting a chat does not delete a file that remains saved in Library."
So a contract you uploaded months ago can still be there after you clear your chat history. Here's how to clear it, and how to never keep it in the first place.
What you need
ChatGPT on the web (Library is in the left sidebar)
A few minutes, once a month
If your account has Space, it takes the place of Library: OpenAI says "If your account has access to Space, Space takes the place of Library."
The clean-up
Open Library from the left sidebar.
Filter by file type: Documents, Spreadsheets or PDFs.
Select the client, HR or finance files you're done with and click Delete (or the trash icon next to the file).
Open Trash (Library, then Trash; OpenAI's help page calls it Recently deleted). On the file, choose Permanently delete, then Delete forever.
OpenAI: "Deleted files are scheduled for permanent deletion from OpenAI systems within 30 days", with exceptions for security or legal obligations.
Files you never want kept
Use a temporary chat for them. OpenAI: "No, files uploaded while using Temporary Chat are not saved to your account or Library."
Good to know
Files from a connected Google Drive can't be deleted from ChatGPT. Delete those in Drive.
In Enterprise, Edu and Healthcare workspaces, Library files follow your workspace's retention policy.
The mistake to avoid
Deleting the chat and assuming the file went with it. Delete the file in Library too.