Thank you for taking the time to visit the Community to report this issue!
If you have not done so already, I would start by signing out and sign back into the Quicken program. To do this, please follow the steps below.
Go to Edit > Preferences > Quicken ID & Cloud Accounts
Click sign in as a different user
Type "yes" to sign out
Once this has been completed, please attempt to update once more and let us know the results.
-Quicken Tyka
Thank you for the response and the additional details.
At this time I would recommend contacting support directly for advanced troubleshooting steps.
https://www.quicken.com/support#contact-support
Quicken Care has the tools to initiate a screen share to view the issue in real-time.
Thank you,