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Email migration from SBS 2011 with Exchange 2010 to Office 365 and autodiscover settings in Outlook

Once you have decided to migrate to Office 365 and all mailboxes are moved to Office 365 you will need to connect Outlook on your desktops and laptops to Office 365. If you try doing that without any changes on your SBS 2011 it will fail. The reason for this is that on Exchange 2010 we have something that is called a  ‘autodiscover virtual directory’.

As soon as Outlook starts up inside an SBS Lan it will look for autodiscover settings on your server and connect to the Exchange Server running on your SBS 2011 and that is what you do not want.

On the SBS we run Remove-AutodiscoverVirtualDirectory to remove the virtual directory that causes the unwanted behavior but first we need to figure out what the identity is of that directory. We do that by running Get-AutodiscoverVirtualDirectory | fl Name, Server, InternalUrl, ExternalUrl, Identity from within Exchange Management shell.

  1. Start an elevated Exchange Management shell from the start menu.
    Email migration from SBS 2011 with Exchange 2010 to Office 365 and autodiscover settings in Outlook Email migration from SBS 2011 with Exchange 2010 to Office 365 and autodiscover settings in Outlook
  2. Run Get-AutodiscoverVirtualDirectory | fl Name, Server, InternalUrl, ExternalUrl, Identity and copy the identity to a text file. In our case that is “ADATUMSERVER\Autodiscover (Default Web Site)”
    Email migration from SBS 2011 with Exchange 2010 to Office 365 and autodiscover settings in Outlook
  3. Before we continue I want to make a backup of the IIS configuration so we can return to the situation where the virtual directory is still in place. Open an elevated command prompt from the Start Menu.
    Email migration from SBS 2011 with Exchange 2010 to Office 365 and autodiscover settings in Outlook
  4. Run %windir%\system32\inetsrv\appcmd.exe add backup "Before Removing Autodiscover". That will create a backup that can easily be restored. If you ever need to restore your backup read this http://blogs.iis.net/bills/how-to-backup-restore-iis7-configuration.
    Email migration from SBS 2011 with Exchange 2010 to Office 365 and autodiscover settings in Outlook
  5. Now that we have made our backup we can delete the virtual directory by running Remove-AutodiscoverVirtualDirectory –Identity "ADATUMSERVER\Autodiscover (Default Web Site)"
    Email migration from SBS 2011 with Exchange 2010 to Office 365 and autodiscover settings in Outlook
  6. Just a quick check if it is really gone: Get-AutodiscoverVirtualDirectory | fl Name, Server, InternalUrl, ExternalUrl, Identity and see it is gone. If you can I would reboot the SBS just to be sure.
    Email migration from SBS 2011 with Exchange 2010 to Office 365 and autodiscover settings in Outlook

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