Thank you for taking the time to visit the Community and report this issue, though I apologize that you are experiencing this.
Are either of you getting any errors when trying to perform the One Step Update for USAA? Or is this a situation where it seems to go through the updating process, but doesn't bring in new transactions?
For @Rex Adams, I do see that a couple of your USAA accounts have an "Invalid Credentials" status on them. If this is the case, save a backup. Disconnect all USAA accounts (if any are connected), and re-connect them. To disconnect, you choose an account from the list on the left, then click on "settings" in the bottom right of the register. next, click on the "downloads" tab, and then click on "Disconnect Account".
After all of the accounts have been disconnected, we will now need to reconnect them.
For reconnecting we will use the plus sign, in the top left of your Quicken. Then you need to choose the account type.
Now you can choose USAA from the financial institution list.
Click "Continue" in the bottom right. Now you will be prompted for your Access ID & PIN. If you are not sure what it is, click "Get Access ID & PIN", and you will be directed to the USAA website. There they will provide it to you.
For you, @glovesf15,
I don't see that you have any connected accounts with USAA. So you can do the same steps, but you will start with the plus sign (+).
Feel free to update us with any other questions or concerns along the way.