Hello @David Green
Thank you for reaching out to the Community regarding your issue. I would double-check to make sure the payees are the same. Another thing might be trying to match the transactions by disabling automatic entry in the register one month then attempting again the next month once it's been matched. I'll leave more information about it down below.
https://www.quicken.com/support/handling-downloaded-transactions
If you have any questions please let us know and we'll answer once we get the chance!
Thanks,
Quicken Francisco