Hi Laurie, Welcome to the Atlassian Community! I hope you're enjoying Trello.
It sounds like the user might be trying to upload a file that exceeds the size limit. For free users, the file upload limit is 10 MB per attachment, while paid members have a limit of 250 MB per attachment. Please note that the 10 MB limit applies only to files uploaded directly from a computer, not to files attached via a link.
Could you find out if they encounter any error messages when trying to upload their files? Also, do you know the size of the files they're attempting to upload and whether the board in question belongs to a Free or Premium Workspace?
Additionally, it might be helpful to ask them to try uploading from a different network to rule out any connection issues.
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