Thanks for the additional info @TJ_WaterMan.
I can’t seem to be able to reproduce on my end, I’ve asked some colleagues to give it a go too and they were able to successfully attach documents to their tasks. So I suspect this issue is somehow specific to your account. I would recommend reaching out directly to our support team who has better tools to troubleshoot this type of issue.
Feel free to share the URL of this thread so you don’t have to re-explain everything you just said here, and if you could possibly send them a screencast of the issue, it would be super helpful too!
If you don’t already use a tool to record screencasts, Loom is a great app for video screencasts: https://www.useloom.com/
I would also recommend including the entire browser window, including URL bar, in your video video, just to make sure our team has everything they need to investigate this issue.
So sorry for not being able to help further via this forum with this specific issue! I hope this gets resolved asap!