Hello @Dave B.
you for reaching out on the community and telling us about your issue. I do
apologize for the issue you're having. I'm wondering if it thinks you may not be signed in each time. To start off here lets try signing out and signing in to see what we're able to find out. You can do so by going across the top to Quicken > Sign Out. Once you've signed out sign back into your Quicken account.
Once you've had a chance to try this see if you're able to update the accounts without needing to do the sign in each time. If it's still popping up let us know and we'll take another look.