Payments from payment accounts not offsetting in Chase and AmEx payee accounts

Cascadia Rocks

Since November 2022, payments to Chase made from B of A have not offset the Quicken balance due Chase, even though the "online" balance is correct. I now have the same issue with an AmEx account. The B of A account properly reflects the payments, but do not reduce the Chase or Amex balances. Further, as of this morning, the B of A account balance is off significantly.

I have engaged chat assistance on two occasions, the first ending after over an hour when I had to take a business call. The most recent chat this AM ended with the CS person asking if they could call me. nearly 2 hours later I am still waiting for that call.

I have low expectations of assistance in chat; both suggested I just record the entries manually. If I wanted to do this manually, I would not have Quicken.

UKR

If you have issues with transfer transactions not being generated correctly:

For best results manually enter transfer transactions into your register BEFORE you download transactions from the bank which contain the transfer confirmations. For recurring transfers use scheduled reminders and enter them a day or two before the due date.
Be sure to use distinct Payee Names for each transfer / credit card payment to avoid confusing Quicken - memorized payee entries.
That takes the guesswork out of the download process. Because a correctly entered transfer transaction already exists in your account registers, the download process should just match the downloaded transfer transaction to the existing one in both accounts.

Cascadia Rocks

I should have been more clear. I have not had to do any manual entry for 18 months prior to the issue arising. Something occurred in October or November that changed that.