Quicken will list the most recently opened data files, with a checkmark next to the file you are currently viewing.
Let us know how it goes!
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 review and research this issue further.
Thank you,
-Quicken Tyka