I think it might be an issue with that password manager solution as it works fine with mine (Dashlane) .
Maybe others can confirm for the other popular ones…
I don’t have “remember me” box ticked because above Password manager negates need for it . Yours should do to , otherwise its probably not a very good solution if it still requires you to store passwords in browser and other caches.
That aside , when you do an update in some circumstances it does still need password to be rediscovered for me (Probably the interaction is a bit different then) . but in general not.