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Outlook cannot contact Autodiscover from Office 365 environment, during a transition from a SBS 2008 server.

Here you find a powershell script which was very useful for me.

All scripts are free of charge, use them at your own risk :


When you have a network with an Exchange 2007 server or higher, sometimes your Outlook is not able to connect to the autodiscover settings, as placed in your external DNS. This is a well know issue when migrating from Small Business Server 2008 (SBS2008).

The solution for this is to remove the Autodiscover Virtual Directory settings, on the old SBS 2008 server.

This problem commenly apears when you have a migration from SBS 2008 to Microsoft Office 365 (Exchange Online), because outlook still want’s to connect to the old SBS 2008 server, which is not used for e-mail anymore.

Here you’ll find the solution for connecting your outlook to the Office 365 autodiscover option:

Note: Use the Exchange PowerShell Console with a elevated prompt!

1. Open the elevated command prompt and back up the IIS configuration (explained here):

%windir%\system32\inetsrv\appcmd.exe add backup “Backup Autodiscover”

2. Open an elevated Exchange Management Shell and retrieve the current autodiscover virtual directory:

Get-AutodiscoverVirtualDirectory | fl Name, Server, InternalUrl, Identity

3. In the Exchange Management Shell, remove the autodiscover virtual directory:

Remove-AutodiscoverVirtualDirectory –Identity <identity value retrieved above>

Note: When you have spaces in the indentity use braces like the example “Backup Autodiscover”

You will have to confirm by typing a “Y or A”.

4. Check that the autodiscover virtual directory is removed:

Get-AutodiscoverVirtualDirectory | fl Name, Server, InternalUrl, Identity

This should now return nothing!

5. Now, with Outlook running on a desktop, hold the Ctrl button, right-click on the Outlook icon in the system tray, and select Test E-mail AutoConfiguration. Enter your email address and password and click the Test button. The results should come from the Office 365 server.

6. Now you can configure your Outlook client to use Exchange Online.

1 comment to Outlook cannot contact Autodiscover from Office 365 environment, during a transition from a SBS 2008 server.

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