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So we recently upgraded our on premises server exchange 2013 to the latest roll-up, I also think its important to note that, we use office 365 for various things (but not email obviously)

Mobile Phone Mail, Web Mail client (OWA) ALL WORK!? using the on premises exchange 2013 server so I know it works, Also The windows 10 built in mail client works!?

This is a serious mystery to me I have been working on it for days, the boss is NOT happy, and every day that goes by I fear for my life (joke)

But seriously there must be a reason this is happening. Why does it work for everything EXCEPT MICROSOFT OUTLOOK?!

Why does it prompt us twice for passwords and it goes like this: First time , it prompts us, we put in email and password, and it goes through no problem Second prompt , (kind of looks like a Microsoft Account prompt to me) that does not go through and prevents us from accessing our email.

PLEASE HELP ME ASAP I WILL BE FOREVER GRATEFUL!

pulling hair out - thank you tom

draftdis
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    kort3x is on the money. This is most likely O365 priority in Autodiscover. You can disable this behavior via Group Policy for domain joined machines by using the Office ADMX templates or via GPP registry changes. - https://support.microsoft.com/en-us/help/3211279/outlook-2016-implementation-of-autodiscover. – joeqwerty May 10 '20 at 23:57

2 Answers2

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Sounds like an Autodiscover issue to me.

Have you checked your virtual directories, dns, certificates, etc?

kort3x
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    also: If you have added your domain to O365 be aware that newer Outlooks prioritize O365. https://support.microsoft.com/en-us/help/3211279/outlook-2016-implementation-of-autodiscover – kort3x May 10 '20 at 23:09
  • Have you cheked what method Outlook is using for Autodiscover? See here under "More information": https://docs.microsoft.com/en-us/outlook/troubleshoot/domain-management/unexpected-autodiscover-behavior – kort3x May 10 '20 at 23:19
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Does this issue happen to all users? what errors you got when it prevents from accessing mails?

Run EXRCA to test Autodiscover, there are more details for your reference.

Have you tried to create outlook profiles for these users?

You could run outlook in safe mode to check if this issue continues.

Joy Zhang
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