Downloaded transactions matching to older/not same payee

Are you automatically accepting downloaded transactions into your registers?

If you are relying on Quicken to "automagically" fill your account registers from downloaded transactions, you may run into problems. Despite all efforts by the Quicken programmers, the "Autopilot" (that's my name for the part of the Quicken program which processes downloaded transactions and converts them into new register transactions) is not infallible. For that process to work 100% of the time one would need a crystal ball because the information downloaded from the banks often is just too terse and cryptic.
You should, at least for a while, turn off the "automatically accept downloaded transactions into registers" setting to gain better control over what is downloaded and what to do with it. Click on and review each downloaded transaction, make changes if necessary before you click to accept each transaction.
Any changes you make to downloaded Payee Names are remembered in Renaming Rules.
Any other changes you make (add/change Category or Memo text) are remembered in the Memorized Payee List.

Next time the same transaction for this Payee comes along, Quicken should remember and give you a better new register transaction.

Where are the "Auto-accept downloaded transaction" settings?
There are two places where this is controlled in Quicken for Windows:

• Globally, for all accounts, in Edit / Preferences / Downloaded Transactions
• For each account individually, the global setting can be overridden from the Edit Account Details screen, Online Services Tab. Look for blue text "Automatic Entry is: ON / OFF". Click the text to change the setting.