Additional assignment-related features and issues within Microsoft Teams for Education
Hi Jordan,
Thanks for reaching us in community!
For this issue, you may let the users to use URL links instead of files in the assignment attachments as a workaround.
We'd like to know if it's a client related issue or not, you can check whether the attachments file can be upload successfully in https://teams.microsoft.com/ or not. If web-side works functioning, it should be a client related-issue.
Meanwhile, please kindly share us a screenshot of the entire failed page, so that we can have a better understanding for such a condition in case missing something.
Best,
Shawn