"I keep up with Vanguard and my checking account with Quicken."What does that mean, exactly? If you routinely do a One Step Update for both Accounts then certainly the transfer should show up in the two Accounts. I'd expect that first the transfer would show up in the "from" Account (Vanguard) and if Quicken couldn't "match" that downloaded amount to something in the Vanguard Account, that you'd enter it as a transfer from Vanguard to Checking at which point the download would "match" and you'd accept it. Then probably a day or two later the One Step Update from the bank would include the transfer in, find a match, and you'd accept it.If you're entering the transfer manually in Quicken when you request the transfer - and that's the better way of going here - then I'd expect that you'd make the entry in the Vanguard Account with the offset being the checking Account. Even if you're not downloading information from the financial institutions that gets both Accounts correctly stated, (ignoring timing differences).