Hi. I'm in a different version than you are. Just reporting my experience.
Has your version offered you American Express via DIRECT CONNECT, which is a relatively new offering vs Express Web Connect ?
On the "Activate One Step Update" dialog, the "show" button in the password entry box has no effect - clicking on it does not show the password vs the ******'s.
If that still doesn't work and if you haven't done
so already, I'd say it's time to call Quicken Support on the phone and request
help. Let them do a screen share session
with you to review the situation on your computer, to determine the nature
of the problem and to figure out how to fix it.
Quicken user since version 2 for DOS, now using QWin Biz & Personal Subscription (US) on Win10 Pro.