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Problem setting up Outlook to Office 365 with Azure AD Sync implemented RRS feed

  • Question

  • Hi guys,

    We're just doing a migration over this weekend and we've implemented Azure AD connect with a brand new DC with with a brand new AD user list. Everything's going great...but we got a weird issue. 

    1) when a user goes to setup an outlook profile, it automatically see's the user's email address and name and tries to search for the settings. It then just sits there and searches but never finds the settings, nor times out. It's doing the same thing as if there was an exchange server on the network and it automatically goes and tries to autodiscover.

    2) we are moving away from an SBS 2011 box. The SBS 2011 box is domain.LAN, new DC is domain.LOCAL. All the machines on the network are connected to the 'new' domain.LOCAL domain and all DNS is pointing to the new DC. Basically, nothing should be referencing the old SBS box. 

    Unfortunately we can't turn off the SBS box just yet as the mail is still being pushed up to the cloud. 

    Does anyone know what might be happening here?

    Also, all the Office 365 DNS records are in there fine and autodiscover is working (tested on iphone).

    Any help would be appreciated! thanks.

    Friday, January 22, 2016 7:37 AM

All replies

  • On a domain joined environment, Outlook will always try to connect to the local server. To work around this, use the reg keys detailed in this article: http://support.microsoft.com/kb/2212902. All you need working for O365 is the HTTP redirect method (CNAME), you can block the rest.

    Apart from that, make sure to update your Office clients to the latest version, if using Outlook 2016 in particular there was a nasty bug with autodiscover trying the same endpoint for 15 times or so before giving up, which means you had to wait for 10+ minutes before it moves to the next method. If using Outlook 2007, you need to run the desktop setup wizard from the O365 portal first.

    • Proposed as answer by Arvind S. Iyer Sunday, January 24, 2016 11:19 AM
    Friday, January 22, 2016 8:23 AM
  • Thanks! That's helped!

    I ended up having to create a group policy to add registry records to everyone's machines to exclude all but HTTP redirect method. After I added those, it uses the HTTP redirect method and all is well.

    It's weird that this has happened as it's happened on Outlook 2013 and Outlook 2016 and it hasn't happened at any other sites where we have dirsync setup. The only thing that's different is that this is our first client with Azure AD Sync as opposed to Dirsync. It's really strange that we've never seen this before with 365 and domain joined PCs.

    Hope this helps someone else!

    Sunday, January 24, 2016 2:37 AM