I have an automatic transaction which is scheduled on the 2nd day of every month to transfer money from an investment account to a checking account. For months when the downloaded transaction from the investment company is dated on the 2nd or later I simply accept the transaction and all is well. However when the downloaded transaction is dated before the 2nd what I have done is change the date of the transaction in the Quicken register so that the downloaded transaction matches. Then I accept it. But when I switch over to the checking account the transaction has been changed from a deposit to a payment. Obviously the money can't flow both ways! Simply changing it back to a deposit seems to work without any complaint from Quicken. Nevertheless this should not be happening.