It's nice to see you here today, @jlk2021,

When you connect your bank for online banking, the system tries to match them with transactions you've already entered into QuickBooks. We use the Date, Description, Payee, and amount spent or received to get the entries automatically matched.

If there are elements that will not trigger the auto-match option, the system will let you do it manually. This is the method you've been trying to do.

However, since you mentioned that this has worked before and for some reason it's not doing it now, I recommend contacting our QuickBooks Mac Support. Our representatives can help check on this and if possible get this reported to our engineers.

To contact our support, click this link to initiate a live session: QuickBooks Desktop for Mac chat

Let me know how it goes. I want to keep track of this banking topic and make sure it gets taken care of. I'm also here if you ever need further help with any other things in QuickBooks. Have a good one!