One Payee/Payor and Two Categories

molechaser

I have an organization that monthly debits my bank account for a life insurance premium, and twice montly direct deposits IRA payments as retirement income. Since they are the same payee they all come into my bank categorized as life insurance premiums. Is there a way to have the IRA payments automatically be categorized as retirement income?

UKR

Have Scheduled Reminders set up in your checking account, each with a distinct Payee Name,
e.g., "XYZ {life insurance}" and "XYZ {retirement income}" and categorize each as to your needs.
Set these reminders to automatically enter a day or two before their due date so that you have proper register transactions. When you download transactions from the bank after the due date, the downloaded information will be matched to the already existing register transactions and everything should be fine.

splasher

@molechaser Also, is there anything different between the combination of the Downloaded Payee+Downloaded Memo of the two transactions?

If so, you could create Renaming Rules based on that difference to rename the downloaded payee which could then match to the transactions created by reminders as suggested by @UKR which you should do regardless if there is a difference or not.