"New" transactions are not recognized when entered into register

Hello,
When I download transactions, any that were not already in my register, are correctly labeled, "new." Once I enter the transaction, Quicken should automatically "Match" them, but it is no longer doing that. This problem began after the most recent update; that could just be coincidence, but I'm not certain.

I understand that some new transactions have to be manually matched, but in the 15-ish years I've used Quicken, that has only happened when my bank sends a check on my behalf. I now have to manually match every single transaction unless it was already in my register when I downloaded from my bank (or credit card).

One other caveat - if I close Quicken and re-open it, then it will match the transactions.

Did a setting get changed of which I am unaware?

Thank you,