Upgrade Win 2012 R2 VM to win server 2016 breaks Exchange 2013

exchange-2013windows-server-2016

I Just upgraded my Win Server 2012 R2 VM hosting Exchange 2013 to Win Server 2016. After the upgrade completed (with no errors) and I rebooted, Many Exchange services failed to start. When I look at the first error in the Application log, it indicates the following:

Process Microsoft.Exchange.Directory.TopologyService.exe (PID=4496).
Microsoft Exchange Active Directory Topology Service failed to start.
Exception details:
Microsoft.Exchange.Data.Directory.CannotGetSiteInfoException: Could
not find information about the local site. This can be caused by
incorrect configuration of subnets or sites or by replication latency.
at
Microsoft.Exchange.Data.Directory.NativeHelpers.GetSiteNameHookable(Boolean
throwOnErrorNoSite)    at
Microsoft.Exchange.Directory.TopologyService.TopologyServiceMain.CheckCriticalDependencies(String[]
args)    at
Microsoft.Exchange.Directory.TopologyService.TopologyServiceMain.OnStartInternal(String[]
args)

The failure of the Active Directory Topology service to start prevented all the other Exchange services from starting, so I'm guessing this is the root of the issue.
So what do they mean by "incorrect configuration of subnets or sites"? what should I look at next ?

NOTE, I did run ADPrep /ForestPrep and AdPrep /DomainPrep before the OS upgrade

Best Answer

I am glad you said this was a dev environment, otherwise this is a résumé generating event. You have made a number of assumptions with no backing, not even past history of Microsoft to back them up, particularly as there is plenty of evidence to say that your assumptions were wrong.

  • In place upgrades of the OS with Exchange installed have never been supported. If you want to upgrade the OS then you build a new server and migrate. It has always been that way.
  • For that matter, in place upgrade of Exchange from one version to another isn't possible either, so this task seems pointless.
  • The documentation for Exchange is not static. The fact that it doesn't mention Windows 2016 doesn't mean they are ignoring it on the Exchange 2013 documentation. Presuming they have tested it and made it ready for release when the OS is released is naïve at best.
  • The Exchange product team have actually said that Windows 2016 will not be a supported OS for Exchange 2013 - almost a month ago. September 2016 Quarterly Exchange Updates – You Had Me At EHLO… | The Microsoft Exchange Team Blog

You are basically completely unsupported and have a huge mess on your hands.

However, lets not waste your stupidity on failing to check even the basics, as now you can practise DR to clean up the mess. Take a copy of the databases and power off the machine. Reset the computer account (DO NOT DELETE), then reinstall Windows 2012 R2. Give the machine the same name, install the basic requirements (netframwork 4.5.2) and then install Exchange using the recoverserver switch from the command line. It should recover, allowing you to rebuild the environment correctly.

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