Hey @greenwellmfg,

Are you having the same problem with QuickBooks Desktop, or QuickBooks Online.

If it's the prior, I would do the following:

1. Make sure your software is up to date.

2. Try adding an attachment again.

3.  If that still doesn't work,  Backup your system file so you always have a save point. Then,  download File Doctor and let it do a diagnostic of your software. This should automatically correct most problems.

Let us know if that does the trick.