Exchange 2010 Hybrid – upgrade to 2016 before or after

I’ve lost count at how many migrations I’ve done now into Office 365, varying from Exchange 2003 all the way to Exchange 2016 however each time I do a migration I will always recommend that the customer users the Hybrid migration method, whether its with Password Sync, ADFS or some other means of authentication the migration process is still the same.  The customers who run Exchange 2003, yes there are still companies out there running it I would need to put in a 2010 Hybrid server, customers running Exchange 2007 I’d put in a 2013 Hybrid server and Microsoft provided the hybrid licenses free of charge for those very reasons. However what about if you’re running Exchange 2010?  The hybrid license did not cover this before Exchange 2016 was released. My personal thoughts are its Hybrid ready so you do not need to deploy a new Hybrid server any way. However, now with Exchange 2016 it seems tempting to install a new shiny 2016 Exchange Hybrid server in the Exchange 2010/2013 environment for the hybrid role.

The licensing terms for the Hybrid server were pretty clear cut before Exchange 2016:


Microsoft, now provide you with an Exchange 2010/2013/2016 Hybrid License Key so what’s the deal here?

I came across this article about the 2010/2013/2016 Licensing to clarify things:

So the way I understand that is Microsoft now provide the Hybrid license free regardless of your current infrastructure setup.

Looks pretty good! So that would mean you could deploy an Exchange 2016 Hybrid server in your Exchange 2010/2013 environment. Sure that’s great, but there are a a few things to consider before going ahead and deploying your new server. The 2 main questions I ask my customers are:

  1. Are you running a Load Balanced front end environment? if yes then cutting over to one frontend server would give you a single point of failure or are you going to deploy multiple new 2016 servers?
  2. Is it really worth installing a 2016 before you migrate? The Hybrid Configuration Wizard was designed to run on Exchange 2010/2013 and 2016 so why add risk to your migration by introducing extra complexity, deploy the Exchange 2016 server at the end of the migration reducing the risk and impact to users.

I’m a fan of making use of what you have to achieve the task, but, for me, the key thing is Exchange 2010 SP3 is still supported for hybrid and for me it goes to the old saying “if it ain’t broke don’t fix it”.

There are some times when installing an additional Server for the migration maybe be required, I’ve worked with customers who have had a 3rd party hosting their Exchange, which is a separate site within their AD and due to network issues/patching issues it was not possible to configure the hybrid against the servers, so a new Exchange server was deployed at their own site with a new public URL ( as opposed to using for example) and the migrations were all done through that endpoint. This then meant they could serve notice to the 3rd party once the migrations were complete and still maintain the management capabilities.

All I would say is take a second to re-evaluate the need of installing your new 2016 server before jumping the gun and deploying it if you’re running Exchange 2010 or 2013.

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