Windows 10: Weird Outlook login/authentication behavior.

Ok, so "weird" is kind of vague, so here's what's going on...

Recently added a user's work email to their outlook which requires not just their email, but also their domain/user, due to how their email system is set up using just the email and pass get's a reject from the system.

As I mentioned I was successful in adding the account but Outlook is acting somewhat bizarre in that it's prompting for the user to provide their credentials every so often including when launching outlook BUT the popup window doesn't allow the input of the domain/username, only the email address and pass, resulting in the system rejecting the submitted information as I mentioned just a moment ago.

Considering I opted for outlook remembering the user's credentials, it baffles me that it's prompting for that information.

But wait, it gets better...

So if you close the pop-up prompt instead of trying to supply the credentials, Outlook starts to update the mailbox for a moment before it stops and then displays "Need password" in the bottom gray status bar.


Bizarrely still is that if you just click the "Need password" in the status bar, no prompts pop up and Outlook goes back on it's merry way in updating the mailbox.

I need someone's help in deciphering this madness and what if anything I can do to stop Outlook from prompting for those credentials...

Sincerely,
James

:)

 

Windows Microsoft account authentication

I have a valid Microsoft account and a Windows 10 PC with Hello/PIN account login enabled. I also have the Microsoft Authenticator app installed on an iPhone and configured for the Microsoft account. Additionally, I have two step authentication configured
for the Microsoft account. With all of that said, I have become very exasperated while trying to unravel the various authentication paths (and their security implications) through this multi level login security scheme. I find the associated account security
documentation to be woefully inadequate. Thus, I would like to pose the following list of questions for starters.

1. Does Windows Hello/PIN amount to a two step verification login procedure for my Microsoft account?

2. Does approving a Microsoft Authenticator login attempt (without two step verification explicitly set up)

amount to a two step verification login procedure for my Microsoft account?

3. Does approving a Microsoft Authenticator login attempt (with two step verification explicitly set up)

amount to a two step verification login procedure for my Microsoft account?

4. If answers to both 2 and 3 are yes, then what does explicit set up of two step authentication do?

5. Does a coherent, comprehensive document explaining Microsoft account security configuration exist somewhere?

6. If the answer to 5 is yes, wherer is it?

Thanks in advance.

 

Authenticator App

Hello, I would like to suggest to add a feature in the Microsoft authenticator application which enables the user to login into a session without using a password just like outlook or other Microsoft's services.

 

Microsoft Officially Launches Outlook.com

Outlook e-mail does not have Multi-factor authentication in the strictest sense - at least when compared to GMail. However if you try to change anything "personal" about your Microsoft/Live account, then it will ask for a temp code it texts to your phone.

So, yes and no in regards to your question. No, it doesn't require two-factor authentication to log-in, but if you go and try your change some "critical" account settings, it will ask you for a second step of verification. However, in regards to whether the e-mail service specifically offers two-step authentication for login; the answer would be no.