Getting Outlook Autodiscover to work properly.....

LockDown32
LockDown32 used Ask the Experts™
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I just migrated a SBS 2011 server to a 2019 Standard. All the email accounts were moved to Office 365. The old SBS Server is offline and has been for a month now. The problem is that when I try and set up Outlook for a new user it is still trying to use, and the auto discover still points to, the old SBS Exchange Server. This is a nightmare. How can I get Autodiscover to work properly?

   As a footnote the even changed email domains. When they had the Exchange server all their emails were @olddomain and when they went with the new server they went with a new email domain @newdomain.
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Commented:
Just for the sake of completion, please check the DNS records internally for

autodiscover.newdomain.com

checked against a lookup to Googl'es DNS (8.8.8.8)

It _should_ point to the correct address (a MS hosted one).
LockDown32Owner
Top Expert 2016

Author

Commented:
Internally there is no autodiscover in the DNS. There isn't even a forward lookup zone for their email domain.

With Office 365 Microsoft just has you use autodiscover.outlook.com in the public DNS so there isn't really a autodiscover.newdomain.com is there?
Most Valuable Expert 2015
Distinguished Expert 2018

Commented:
Exchange 2010 and above configure an autodiscover SCP record, and apart from that you should check for any remaining internal DNS entries and remove or point them to O365. Apart from that, if you want a client-side solution you can deploy the reg keys detailed in this article: https://support.microsoft.com/en-us/help/3211279/outlook-2016-implementation-of-autodiscover

All you need working for O365 is the HTTP redirect (CNAME) method, you can block all others.
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Mark BillExchange, AD, SQL, VMware, HPE, 3PAR, FUD, Anti MS Tekhnet, Pro EE, #1

Commented:
Ews editor for autodiscover viewer testing. This is a lifesaving tip.

When we run https://autodiscoverurl.contoso.com/autodiscover/autodiscover.xml on the affected users of do you get error 600 which equals success? If not you have dns problem possibly pointing wrong place.

Could also be SCP issue so use EWS editor to find out whether it's DNS or SCP.

Clearly autodiscover is setup incorrectly knowingly or unknowingly .

Let's remember a computers location defines which AD and Exchange forest we are looking at for autodiscover.

Exchange test autodiscover results cmdlets as affected user?
Mark BillExchange, AD, SQL, VMware, HPE, 3PAR, FUD, Anti MS Tekhnet, Pro EE, #1

Commented:
To further expand if .xml test equals error 600 which means it's working! You almost certainly have a SCP issue.

Exchange BPA would not hurt here either.
LockDown32Owner
Top Expert 2016

Author

Commented:
https://autodiscoverurl.contoso.com/autodiscover/autodiscover.xml yields page not found (and I did replace costco.com with their email domain)

I think I need to point out again that the Exchange Server is offline

I did run the Remote Connectivity Analyzer for Office 365 and selected the "Outlook Autodiscover". It passed. So any ideas why I automatic setup doesn't work?
LockDown32Owner
Top Expert 2016

Author

Commented:
Thanks all. It appears as though it was working properly. Microsoft has issues with Office 365 during the period I was trying it. Once Microsoft got their side fixed it seem to work OK.

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