Outlook email keeps prompting for a password, and then not accept it. Blocked out of emails.

Vince try this post and see if this works for you

https://answers.microsoft.com/en-us/outlook_com/forum/outlk_win-outtop_classic-outsub_ofh/outlook-classic-and-popgmail/52d8d787-60d2-4644-9279-67779b1996be?messageId=8fa3a740-2554-4544-acb2-094e49963816

I have tried everything, I can't believe I've had this issue for a month and I can't believe that I'm unable to speak to any to a human at Microsoft.

The problem is with my iPhone. Shortly after a recent "update", I was logged out of email on my iPhone. I did NOT actually log out, I suspect the recent update caused the logging out. I have never logged out of email, on my Desktop, Laptop, or iPhone. The problem is that it will NOT accept the password I have been using for a long time, and it will NOT allow me to recall or reset my PW because I have supposedly enabled secondary authorization, which I actually did NOT. I do have the MS Authenticator on my iPhone, l but I have not used it, and sadly, it too will not accept my password, so it is essentially useless. I cannot receive an SMS code from MS either, If they cannot send me an SMS code because I am residing down in the Caribbean, that's a rather poor excuse, as I can receive SMS codes from other US sources. Fortunately, my Desktop and Laptop are still logged in. Tried getting answers from Apple regarding the iPhone, but they claim there's nothing wrong and that my iPhone is operating normally. What a bunch of BS!

I am having a similar issue outlook classic not accepting email and password using pop.gmail. This is happening with 3 of our computers all os a sudden on the same day.

Again, for you and anyone else thinking about replying to that comment, you might want to create a new thread and ask that question again, as that support specialist was asking the original poster for that information.