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Eivind Gussiås LøksethFlag for Norway

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Outlook 2016 reports invalid server certificate for autodiscover.msn.com

I get a security warning from Outlook (desktop app in Windows) about an invalid certificate.

I've had a similar warning on my Android device for weeks, but the warning in Outlook appeared today. On the PC, I can see that autodiscover.msn.com gets a certificate issued to outlook.com.

On the Android device, I just get a suspicious warning about an invalid server certificate.

I don't think there anything I can do to fix this issue. It's probably a redirect issue on the server? My email account is a very old hotmail account on the msn.com domain, and a few years ago I added and outlook.com alias, and later I set that as the primary address for the account. Maybe that's not a very common thing to do.

Also Outlook 2016 has become extremely slow lately, and it hangs and displays disconnected and warning icons. Maybe this behavior is related to the security issue, but I'm not sure.

I've tried removing the account and adding it back - and not only the msn.com/outlook.com account, but all email accounts in Outlook. Didn't make any difference.
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Brian Murphy
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Upon viewing the certificate does it look something like this?
When I checked the record did not see anything unusual.  If you open CMD and check nslookup for that record do you get
autodiscover.msn.com was resolved to 157.55.6.73.

MX is CNAME
CNAME      autodiscover.msn.com      eas-autodiscover.glbdns2.microsoft.com      15 min

But then I see this:
https://answers.microsoft.com/en-us/outlook_com/forum/osecurity-osafe/security-alert-autodiscovermsncom-invalid-or/2f46cd9e-8ffe-4b25-a135-bda214920503
Have you enabled two step authentication and create an app password for your hotmail account?

If no, you need to do it now.

All outlook.com email accounts should have been migrated to Exchange Online and Outlook 2016 must automatically connect all outlook.com email accounts as manual setup is no longer supported.

Remove all outlook.com account in Outlook 2016 and restart computer.

Run Outlook 2016 and add an Exchange account, just input the full email address of your hotmail as user name and the app password as password and Outlook 2016 shall be able to do the setup for you.
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ASKER

@Brian Murphy, I get exactly the same prompt as randy986 replied on August 22, 2017 in the thread you linked to. I accepted the certificate. So far so good, but the Samsung email app on my Android device doesn't give an option to accept the certificate. So I'll have to live with that warning until the certificate issue is fixed server side. A certificate issued to outlook.com is of course not valid for the domain autodiscover.msn.com.
There will be no fix on the server side.

You need to install Outlook for Android app in your Samsung device instead and let the app autocomplete the setup of your hotmail account.
@Jackie Man, Outlook for Android works without any issue. But I had to setup the Samsung apps to sync contacts to the new device. So I guess I have to continue using it to sync new contacts, even if I prefer to use the Outlook for Android app for email.
Please give details on Android OS and whether you have a MDM to deploy the Samsung email apps.
It's a Galaxy S8+ private phone, so no MDM involved. It currently runs Android 7.0 with Samsung Experience version 8.1.

I expected this to be a very common issue, so I googled it, but didn't find anything reported lately - a lot several years back though. That said, I didn't find the thread at answers.microsoft.com either, so there might be other threads that I don't know of. Actually I searched and tried to post the issue at the Microsoft forum, but the submit failed over and over again, so I gave up. I guess I have to report this to Microsoft Support, but I think I'll leave it like this for a while more. The email app works fine even if the security issue persists, so I just have to ignore the message and continue.
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Jackie Man
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Do you still have a problem for Outlook 2016?
I've accepted the certificate on two PCs. It seems to work well so far.
If you have no further question, please do a favor to close this question.

Thanks!