jacobs said: @Chris_QPW You say this is a "sometimes" event, but unless I'm misunderstanding @wstewarttennes, the only "sometimes" part is whether the checking account gets hit for the purchase or not. In terms of Quicken, though, that's not a problem. In all cases, the purchase is recorded in the Venmo account. If there's nothing hitting the checking account, that's call there is to it. If the checking account gets hit, it just needs to be a transfer in Quicken rather than an expense, which is easy to accomplish. (This is unlike PayPal, which will first spend down your PayPal balance and then pull the remainder from checking.)
Chris_QPW said: @jacobs Let me clarify one thing. I wasn't saying that Quicken can't "handle" this situation. I was saying it can't handle it automatically (in all cases) as far as I can see. User intervention is going to have to happen on at least one of these situations.
Chris_QPW said:Unless I'm mistaken Quicken Mac doesn't allow controlling QuickFill by account, correct? Well QuickFill is going to be controlled by the payee/memo. And unless I'm mistaken, the payee is going to be the same whether it hits the Venmo or the checking account.And I might add that this isn't a single payee. So lets say it hits just the Venmo account and the payee is "George". You setup the QuickFill that George gets the category of Dinning. Now the balance of Venmo is to small for your next purchase with George. Now you get two transactions one in the Venmo account and one in the checking account for George. You instantly have two problems. First off George is already mapped to Dinning, so you can't have it automatically pick something else like a transfer in the QuickFill. But there is another problem. If this is just a transfer then you have moved money from your checking account to the Venmo account, but not debited the amount anywhere. Here is where (at least on PayPal) the second problem comes up. There should really be two transactions on the Venmo download. One for the transfer and one for the debit, but there is only one.