This behavior started in May when all the automatic entry reminders got screwed up as well. I have tried multiple things to resolve this issue from these posts:
https://www.quicken.com/support/why-am-i-being-asked-sign-my-quicken-id-repeatedly-or-why-am-i-being-asked-activation-code
These fixes have NOT worked. Is there a fix or workaround to get Quicken to stop asking for the Quicken ID password every single start?
The main discussion on this issue is here:
Thank you. I hadn't found that one when searching. Please lock this thread.