Hello @Andrew Dubin,
Thank you for reaching out to the Quicken Community, though I do apologize that you are experiencing this issue.
To clarify, you have successfully linked your USAA ebiller, however, the status shows as pending and no ebills are downloading?
If so, I suggest deleting and re-adding the USAA ebiller. You can do so by navigating to Bills & Income > Three dots > Unlink ebill. You can then re-add the bill by navigating back through the same pathway and choosing Link ebill then proceeding to login using your normal information.
Please let me know how this goes!
Thank you for coming back to update us.
The USAA migration may have an effect on properly adding your USAA ebiller. However, I think that it would still be a viable option to attempt the troubleshooting steps that I previously gave, if you so choose.
I would also like to confirm that your USAA credit card is currently connected using Quicken Connect?
I look forward to hearing back from you!
I had the same issue and after hours on the phone with tech support they came to the same conclusion, "known issue, working on it" and I'm on a PC, so it isn't your Mac. Hope they fix it soon, or Quicken will loose my business.