For at least a month, I've randomly not been asked to unlock my QMac file on launch with my Apple Watch.
The only solution is to go into Quicken > Settings > Security and uncheck "Allow Apple Watch to unlock this file" (and enter the file password) and then immediately re-check the checkbox (and enter the file password). Quit Quicken, launch again, and prompt for Apple Watch is back.
Are others seeing this issue?