Hey there, brian-zipmessage.
If the system finds the same transaction and needs to be matched, QuickBooks will still apply the rules and require confirmation.
To know more about how bank rules work in QuickBooks Online, check out this article: Set up bank rules to categorize online banking transactions in QuickBooks Online. On the same link, you'll find steps on how to fix a rule if it isn't applying to transactions.
Additionally, you can visit the following link. This will provide you with more information on how to review and match multiple transactions in QuickBooks: Categorize and match online bank transactions in QuickBooks Online.
I'm just around to help if you need further assistance. Take care always. Have a good one!