Hi there, @emifinley.
I appreciate you trying some steps to get this issue sorted out. Allow me to share some troubleshooting steps to get this sorted out.
If you're trying to attach documents from your Doc Center to your company file's transactions and nothing seems to be happening, perform the following steps:
For more details about this process, please visit this article: QuickBooks Attached Documents: FAQs and common issues.
However, if the issue persists after trying these steps I'd suggest giving our Technical Team a call. They have the necessary tools to work with you to find out what exactly may be causing this issue.
To do that:
Keep me posted if there's anything else you need about this concern. I'm always here to help. Have a nice day!