This is driving me absolutely insane as well.  I am going to review the comments here and see what I can figure out tomorrow.  I have spent DAYS on the phone with support and nobody is able to help me figure out why o can’t match transaction.  I even just got an email back about my case that there was nothing they could figure out.  I even had one support person witness the issue occur when he asked me to unmatch one of the only ones in was able to get and then we were unable to get it back.  All of my cash and cash app items are displaying to match my deposits but not any of my card payment deposits and there is nothing different about the way they are set up.  My payroll checks that were run though QuickBooks with the check numbers recorded are even not showing up for me to match.