Windows Security pop up in Outlook

[alexsmith2709]

I've got a client who use M365 (not provided by me, no admin access by anyone on site). Recently 2 of the users keep getting Windows Security password popups in outlook asking to login to their account. This never accepts the password and keeps asking preventing them from using outlook.
They have around 15 users in total, but this is only happening on 2 currently, it was one and then a day or so later the second started.
I have asked them to run this tool https://aka.ms/SaRA-OutlookPwdPrompt and they said it doesnt fix anything (I have not been on site to run it myself yet).
I cant find any reports of any recent updates causing this, so does anyone know what else that can be done to sort this?

They have contacted their M365 provider (its a franchised business and its all done through a company that head office manages) but they havent sorted it since last Thursday so they've asked me if i can help as i provide other support to them.

 

[nlinecomputers]

Time to run SaRA.

 

[TazUk]

Do they have a password policy that forces them to change their passwords every 90 days or whatever and they've expired?

Have they tried logging in via OWA?

 

[callthatgirl]

Do all the Office updates
Do all the Windows updates, even if you have monitoring
Be sure the account is logged into the right account
Be sure the licensing is with the correct account
Restart

If these do not fix it, I'd recommend a password reset.
If that fails, I recommend testing a new profile, sometimes one bad update can jack it up

 

[alexsmith2709]

Thanks all, i'll go to the office and try these things myself next week i think. Lets hope they do actually know their password!

 

[Mick]

They don't happen to have Gmail accounts set up (as well as whatever the boss provides) do they? Have you asked them which account it mentions in the security prompt?

 

[putz]

Which version of Outlook? Outlook 2013 by default doesn't have Modern Auth enabled and you need to modify registry to enable it if the tenant M365 account is enforcing modern auth (security defaults enabled) or has manually disabled basic auth.

Could their password be expired?

Did you verify autodiscover is detecting the correct endpoint for the email domain?

 

[alexsmith2709]

No gmail accounts to my knowledge. They are using Outlook 365. I'm waiting on a response from them when i can go in to check things in person. I dont think its a password expired issue because other devices with the same account are working fine.
As i dont manage this tenant its making life more difficult than it needs to be!

 

[alexsmith2709]

I finally got to solving this problem.
It was not M365, but was a hosted exchange from Rackspace. The password was correct, but when testing with webmail it accepted the password but then asked again for the login details for OWA and then didnt accepted the details on this page. I could log in to other areas of rackspace without issue. Resetting the password fixed the issue.
It was partly caused by the business owner deleting what he thought were old accounts (some were still in use/added to outlook). Because these accounts no longer existed i had to create a new profile and add the account again as i couldnt remove them.
I dont know what caused this issue at rackspace, it happened with some users and not others.

 

[nlinecomputers]

Rackspace. That’s enough explanation. LOL. One of the many vendors that used to be great until they got sold off. Then they went to sh!t.