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I am in the middle of an Exchange 2010 to Office 365 cutover migration and I keep getting errors when trying to create a migration endpoint on Office 365 hence the migration can't progress.

I have successfully completed step one which is to verify the on premises domain and the Office 365 domain but it seems I am stuck on connecting with Outlook Anywhere using each available method on Microsoft Remote Connectivity Analyzer.

The first error message that I am getting when connecting through Microsoft Remote Connectivity Analyzer is that the:

The certificate chain could not be built. You may be missing required intermediate certificate.

On a side note, this works on internal LAN and Outlook clients are able to connect using autodiscover.

The second error message I get, is when trying to connect using:

Test-MigrationServerAvailability -ExchangeOutlookAnywhere -Autodiscover -EmailAddress <email address for on-premises administrator> -Credentials $credentials

on a Exchange Online PowerShell session I am getting:

The migration service failed to detect the migration endpoint using the Autodiscover service.

I just can't understand why the Autodiscover tests won't pass. I am aware that Microsoft Remote Connectivity Analyzer would show error because it misses the root certificate but what should I do in order to have it running properly?

Please note that I am using an internal CA-Server which is the Exchange Server it self so I have self signed certificates.

I wonder, am I missing the big picture here?

For the migration endpoint/batch to work, is it mandatory to have a valid certificate or to be able to use autodiscover?

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A trusted SSL certificate from a trusted 3rd party like Verisign or similar is required to do a cutover migration to Office 365.

This is why you are getting the errors.

You'll have to purchase and install a legitimate trusted certificate from a trusted online CA in order to proceed.

You could probably get by with Comodo's free 90 day cert: https://www.comodo.com/e-commerce/ssl-certificates/free-ssl-certificate.php but I've never run into a situation where we weren't using a true trusted certificate.

  • I have just confirmed that this is the only way to perform a cutover migration and a 3rd party SSL certificate is required. I have accepted the answer, thank you! – archergr Feb 5 '15 at 14:28
  • You can use a free certificate from startssl.com – BlueCompute Feb 11 '15 at 10:22

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