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Office 365 – Unable to Activate Directory Synchronization

Between demos, trials and actual production environments, I’ve probably activated Directory Synchronization on a couple hundred tenants at this point. The process is pretty non-eventful, you add a domain, validate it and click the button that says “Activate”; then it’s on to the fun stuff.
Just when you start to feel like you’ve seen just about everything, technology is quick to bring you back down to earth…
I recently worked with a client that for some odd reason, we could not activate Directory Synchronization in their tenant. After working with support for a couple days, it turned out to be something quite ridiculously simple.

Some Background

The client’s tenant was a trial tenant that had been extended one or more times so the background was a bit of an unknown for me. Other people had access to the tenant so I’m not really clear how it got to the state that it was in.

The Error Message

A large part of the problem was the very poor error returned by Microsoft. When trying to activate via the portal, you received the error below:
Sorry, we can't process your request. We're investigating right now. Please try again later.
Fair enough, the error basically says to try again later and these types of messages pop up from time to time. Unfortunately, hours later, the same error was being returned.
When attempting to activate Directory Synchronization via PowerShell, a similar error was received:
Unable to complete this action. Try again later.
Again, trying later made no difference.

Resolution

As it turns out, in the list of domains registered in the tenant was “tenant.mail.onmicrosoft.com”. This domain is actually provisioned when you activate Directory Synchronization and is also at that time added as an “Accepted Domain” in Exchange Online.
As you might imagine by now, if that domain exists is the lists of domains (however it got there), you cannot activate Directory Synchronization. Removing the domain via “Remove-MsolDomain” allowed us to successfully activate Directory Synchronization and move on.
 
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