Office 365 Outlook - Autodiscover issue when entering second email address to outlook

Hello, so I've spent enough hours to be at my wits end.

I have an outlook setup with office 365 user *** Email address is removed for privacy ***

While setting up *** Email address is removed for privacy *** on same Outlook, received dreaded 'Something went wrong and outlook couldn't set up your account. Please try again. If the problem continues, contact your email administrator' (which is unfortunately me).

After trying usual troubleshooting steps, create new profile, checking if bob's O365 account works on browser (it does), Outlook on different PC (works) and countless other things (everything looks jumbled up now), I came across Test Email Configuration under Notifications area --> Outlook icon --> Press CTRL + click.

When I tried Test Email Configuration utility with *** Email address is removed for privacy ***, it returns with Success on first autodiscover link https://outlook.offce365.com/autodiscover/autodiscover.xml

When I test with *** Email address is removed for privacy *** on same PC , it not only fails (Error code: 0x800c820E) for the autodiscover link above but every variation it tries after that.

So my questions are:

1. why on the same PC, autodiscover works for one user and fails for another.
2. Does "Something went wrong..." have anything to do w/autodiscover (it does seem so)?

FYI... I already tried various registry options. Some didnt work and other didnt exists for me. I rather not mess with registry anyway because if something goes south, I would be giving CPR to the PC instead of working on this issue. 

This usually happens when the user has MFA or App password enabled hence if the app password is enabled then the outlook will not be configured since it requires the App password to be put in

But if the app password has been forgotten you probably might have to create a new app password and also if the MFA is enabled, disable the MFA and then try to configure it

Let me know if it helps

Thanks 

Ankur

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If you have some version/license type of O365 then why post to a 2016 group???????

And when you show an email address in your post, this is what we see *** Email address is removed for privacy *** 

So all in all it doesn't make a lot of sense

I have been researching a lot and other support websites didnt bother to mask it. So I didnt it would here too. I changed it now to make more sense. I posted under Office 365 so not sure what the issue here is

Were you able to follow my questions?

Hi Ankur, Thx. No MFA because I can setup Bob on my personal PC with no issues. As for app password, not sure what you are referring to

I have been researching a lot and other support websites didnt bother to mask it. So I didnt it would here too. I changed it now to make more sense. I posted under Office 365 so not sure what the issue here is