Microsoft Small Business Server to Server Essentials R2: not a smooth transition

Recently I assisted a small business (of around 10 users) with a transition from Small Business Server 2003 to Server Essentials R2.

Small Business Server 2003 had served it well for nearly 10 years. The package includes Windows Server 2003 (based on XP), Exchange, and the rather good firewall and proxy server ISA Server 2004 (the first release had ISA 2000, but you could upgrade).


SBS 2003 actually still does more than enough for this particular business, but it is heading for end of support, and there are some annoyances like Outlook 2013 not working with Exchange 2003. This last problem had already been solved, in this case, by a migration to Office 365 for email. No problem then: simply migrate SBS 2003 to the latest Server 2012 Essentials R2 and everything can continue running sweetly, I thought.

Sever Essentials is an edition designed for up to 25 users / 50 devices and is rather a bargain, since it is cheap and no CALs are required. In the R2 version matters are confused by the existence of a Server Essentials role which lets you install the simplified Essentials dashboard in any edition of Windows Server 2012. The advantage is that you can add as many users as you like; the snag is that you then need CALs in the normal way, so it is substantially more expensive.

Despite the move to Office 365, an on-premise server is still useful in many cases, for example for assigning permissions to network shares. This is also the primary reason for migrating Active Directory, rather than simply dumping the old server and recreating all the users.

The task then was to install Server Essentials 2012 R2, migrate Active Directory to the new server, and remove the old server. An all-Microsoft scenario using products designed for this kind of set-up, should be easy right?

Well, the documentation starts here. The section in TechNet covers both Server 2012 Essentials and the R2 edition, though if you drill down, some of the individual articles apply to one or the other. If you click the post promisingly entitled Migrate from Windows SBS 2003, you notice that it does not list Essentials R2 in the “applies to” list, only the first version, and there is no equivalent for R2.

Hmm, but is it similar? It turns out, not very. The original Server 2012 Essentials has a migration mode and a Migration Preparation Tool which you run on the old server (it seems to run adprep judging by the description, which updates Active Directory in preparation for migration). There is no migration tool nor migration mode in Server 2012 Essentials R2.

So which document does apply? The closest I could find was a general section on Migrate from Previous Versions to Windows Server 2012 R2 Essentials. This says to install Server 2012 Essentials R2 as a replica domain controller. How do you do that?

To install Windows Essentials as a replica Windows Server 2012 R2 domain controller in an existing domain as global catalog, follow instructions in Install a Replica Windows Server 2012 Domain Controller in an Existing Domain (Level 200).

Note the “Level 200” sneaked in there! The article in question is a general technical article for Server 2012 (though in this case equally applicable to R2) aimed at large organisations and full of information that is irrelevant to a tiny 10-user setup, as well as being technically more demanding that you would expect for a small business setup.

Fortunately I know my way around Active Directory to some extent, so I proceeded. Note you have to install the Active Directory role before you can run the relevant PowerShell cmdlets. Of course it did not work though. I got an error message “Unable to perform Exchange Schema Conflict Check.”

This message appears to relate to Exchange, but I think this is incidental. It just happens to be the first check that does not work. I think it was a WMI (Windows Management Instrumentation) issue,  I did not realise this at first though.

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