This issue has been raised a number of times with no resolution. It started some months back with a Quicken Update. I don't know which. I have credit cards, Paypal, Venmo, etc. set up for automatic payment from my checking account. When I download my transactions, Quicken downloads a transfer out of my checking account and another into the credit card account. This worked properly for years. Now, I get a red arrow next to the outgoing transfer with the error message This transaction has one or more invalid transfers. The problem is that Quicken has started enforcing a strict date match for the two transfers. Usually, the outgoing transfer is posted on one date and the incoming one the following day. So they don't match, and it creates this error. Changing the date of one doesn't help. The only fix is to either delete the transaction and enter it again manually, or to manually change the transfer to a different account and then back again. This is so annoying. Quicken Please Fix This!