Hi, bfinfrock.

To better isolate this issue, as an initial step, you may want to open a sample company file and try to attach a file from there. This is to check whether this has something to do with your company file or QuickBooks Program.
 

If you're able to attach a file using the sample file, we can verify and rebuild your data. The data verification process in QuickBooks is a tool that examines the health of your QuickBooks company data file.

To Verify Data:

1. Choose Window at the top, then Close All.
2. Choose File.
3. Click on Utilities.
4. Verify Data.

To Rebuild Data:

1. Choose
2. Click on Utilities.
3. Rebuild Data.
4. You will receive a warning message to backup your company file, press OK.
5. Click OK when you get the message "Rebuild has completed".

To help you organize and keep your accounts documented, see this article for your reference: QuickBooks Document Center: FAQs and common issues.

If you're still getting the same issue, try to repair your QuickBooks Desktop.

I always got you're back if you have any other QuickBooks concerns. You have a wonderful day!