Hello @Alex Elmes
If only one person's boards are hitting the limit, those specific boards are likely sitting in a Free Workspace instead of your paid one. Have them check the workspace name in the board header to verify it is actually tied to your paid subscription.
As a quick workaround, attaching files via a cloud link (like Google Drive or OneDrive) bypasses the direct upload limit completely. If the boards are definitely inside the paid workspace and still failing, it’s likely a backend billing glitch, and you'll need to contact Trello Support to sort it out.
Best,
Arkadiusz🤠
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