Hi MIchelHMC, I have not noticed that behavior. Most of my attachments are single files, but I do attach multiple files quite often. I just tested it and was able to do four at one time. Are you attaching PDFs?

I have noticed that on deposits, there is no Add Attachment link at the bottom of the Edit window, but the attachment dialog does open if I click the word Attachment, or anywhere inside the drag-and-drop rectangle.

I am in the process of handing off our church's bookkeeping duties to a new person, and this is not making training any easier! Thanks for the kind words.