I know this is 2 years later, but I've recently been having the same exact problem - when trying to submit a pdf or docx file, I get "failed to submit - try again". Then I try to upload it to Canvas through OneDrive and Google Drive - OneDrive doesn't accept it and Google Drive cannot submit it to Canvas because it is a "bad format". Switching browsers didn't help either - I tried Firefox, Google Chrome, and Edge but none worked. I couldn't email it through Outlook either and my only saving grace was being able to send it through Gmail! Also, I attempted uploading the same exact file a day later and it worked just fine! I have no idea why this happens and it's been very nerve-wracking with take-home finals...
If anyone has found workarounds/solutions to this, please let me know!
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