Migration from Windows Small Business Server 2011 Standard to Windows Server 2012 Essentials

Migration notes from Windows SBS 2011 Standard to Windows Server 2012 Essentials

As you probably have already found out, Microsoft’s successor for Windows Small Business Server 2011 is no other than Windows 2012 Essentials. Many people have consider this a let down as Windows 2012 Essentials loses a lot of the SBS 2011 premium features such as Microsoft Exchange. This obviously makes sense as many small business might find more value in hosted alternatives as Exchange Online but does make existing customers who have invested in an on premise solution looking puzzled as to what to do. You will also come to realize that Windows Server 2012 Essentials lacks many features from Windows Standard 2012 including Windows Update Services. What all this boils down to for an existing customer is the need to re-evaluate the on premise deployment and perhaps invest in a regular Windows Sever license. If that is the case, getting SA before the deadline might entitle you to a regular copy of Windows and Exchange, which is something you should definitively research if you are interested.

Getting back to the migration aspect, everything is straight forward as noted on Microsoft’s different TechNet guides on migrating from the different environments to Windows Server 2012 Essentials. However, there are a couple of issues I’ve encountered that if mentioned in those guides they are easily overlooked. Below is a list I hope that might help you during a migration:

  • No matter what, do no decommission your old SBS 2011 server until you are 100% sure your environment doesn’t need it. And how do you know? Turn it off and see if anything breaks for a month at least I would say.
  • Outlook clients might not connect to Exchange Server: In my case only new clients were unable to be setup, but I’ve read online other people have experienced their old clients going offline as well. The reason being as noted on this article that the Global Catalog is moved out of the SBS 2011 server causing Exchange server after a reboot to begin acting up.
  • You can´t migrate to Exchange 2013! I was getting ahead of myself and decided I was ready to dump SBS 2011 and move to the greatest and latest Microsoft Servers…. until I couldn´t install Exchange. What happens is that for you to perform an install (let alone a migration) of Exchange 2013 you need your Exchange 2010 Servers to be running SP3. Sure, no problem, let´s go to Microsoft.com and download that service pack! You keep your computers all update anyway so your probably have it right? WRONG! Exchange 2010 Service Pack 3 has not been released yet, and I read on forums ETA is Summer 2013! I wasted ours trying to install Exchange 2013 just for that. So now I´m simply installing Exchange 2010 on a different machine to have that host my email until SP3 is released but What A Pain Microsoft! I don’t want to migrate to Exchange 2010 to then Exchange 2013!

For now that is all I have. I hope this helps people out there migrating and deciding what to do with their existing infrastructure. I believe the Software Assurance option for SBS 2011 Standard poses a great value for companies looking for an upgrade. All the best!

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7 Responses

  1. Zach says:

    When you migrate to 2012 Essentials, did it bring all the bloat along with it or just the AD? Specifically, I want to get far away from Windows Update Services from managing the Windows Updates on my network. Also, if I’m going to install Exchange 2010 on a second copy of Windows Server (joined to my domain) is it easy to get everything set up and migrated over? Not worried about going to SP3/2013 for now but I definitely want to decrease my company’s email downtime as much as possible, and I’ve never done this procedure before. Thanks!

    • JCarlos says:

      Basically all it lets you do if my memory serves me right is bring over the AD roles/settings/etc. Unfortunately (for some of us) Essentials does not support WSUS out of the box, I had to install WSUS on another machine. So I guess that is a plus for you, but be sure to modify your group policy for your clients to start looking again on the internet for updates. Regarding Exchange the migration is not as easy as I would have liked. I wrote an article on that migration as well and although it is not a next, next, next scenario, if you follow the guide you should be 90+% set. There were two weird things you have to migrate over besides the mailboxes which threw me off until I figured out the commands, which I mentioned in the guide so you should be good. Regarding your downtime issue, you probably want to look at having two Exchange servers or using Exchange Online… not sure what your enterprise requirements are. I happen to sell Exchange hosted seats if you are interested and could offer more details, but if your company wants to have it all inside their network then I would suggest having more than one server for redundancy and load balancing (depending on the size of your deployment). At least having it on a separate box should decrease the number of reboots, Good luck!

  2. Zach says:

    Thanks for your reply. I’ll look for your Exchange migration guide. I wish we could use hosted exhchange but I think they want to keep everything localized… unless I can convince them otherwise. We would need to set up an SMTP relay because we have devices that need to send unauthenticated mail, and I know there aren’t any hosted solutions that want anything to do with that.

    • JCarlos says:

      You can go with a hybrid solution (which Microsoft & Exchange 2013 support), that way you can still have a SMTP server in house, if not a smart host/relay as you pointed out would be needed. There are ones that would work anonymously as long as the request comes from a specific static address.

      The other thing is first I thought you wanted minimum downtime in general with Exchange (so I suggested hosted/hybrid) but now that I read it again you mean just during e migration process right? Well, because you don’t take offline your first exchange server you don’t actually face much downtime. When you are moving your user mailboxes the mailbox being transferred might be offline but the emails being received remain in the queue. After that you just start pointing all traffic to the new server. In general no matter where your mailbox is as they are both front end servers the email keeps flowing. So in my experience the only downtime is during the mailbox transfer. I wouldn’t decommission the old exchange server for a few days/ weeks until all the mail clients have picked up the new server and automatically switch over.. Otherwise they will have to be manually reconfigured (or forced to auto discover). Good luck!

    • JCarlos says:

      Oh, and don’t forget to set up anti-spam on your network. I had my Edge Server do it but I when I setup my Exchange 2013 to receive email I forgot about that… so I ended up getting a lot of SPAM and sending out SPAM. Mostly it was non deliverable emails being sent back to fake email addresses so after enabling anti-spam the SenderID took care of refusing all those emails. If you don’t have a solution in place you either keep your Exchange Edge server or enable Anti spam on Exchange via the shell: http://technet.microsoft.com/en-us/library/bb123559(v=exchg.150).aspx. Hope this helps!

  3. Lars says:

    Hi! Now that Exchange 2013 CU1 and the rollup for 2007 is ready, I’m thinking of performing the upgrade. Scenario is SBS2008-migration to 2012 Essentials (on physical server) and Exchange 2013 on a virtual server.

    But I cannot find a complete guide for this anywhere. I can find guides on Exchange 2007 -> 2013-migration, but not on how to perform this for SBS2008. The migration guide for SBS says nothing about when and how to migrate the Exchange itself.

    Could I simply install Exchange 2013, make it coexist with 2007 for a little while, then when all users are migrated uninstall Exchange from SBS? And then start migration of the SBS itself?


    – Install Exchange 2013 on a Win2012-server joined to the SBS2008-domain
    – Integrate with Exchange 2007, migrate all users
    – Uninstall Exchange 2007 from SBS2008
    – Be happy for a while

    – Start migration of SBS2008 to Essentials 2012 and eventually remove the SBS2008 within three weeks.

    • Carlos says:


      I would probably base myself on the SBS2011 to Essentials 2012 guide. Based on that, you migrate Exchange almost at the end… although I don’t see why that would matter much. Either way I think it would work, but I would first do the migration of the Domain Controller to replicate what they have suggested for the 2011 to 2012 guide. I think you are in the right path, specially with the whole “be happy for a while”. Microsoft recomends keeping your old server pretty much the whole month grace you are given when it is demoted and you are migrating. You could also save the HD where you have your 2008 server for another while in case you missed something… like the shared user folders, maybe some obscure email account (if you migrate properly you cannot uninstall exchange until all mailboxes are out of the system, at least 2010 didn’t let me), transfer of the Global Catalog, demoting of the server, a DFS share, who knows…. the list gets big. I still have my old HD but those far all good! I would recommend doing a backup before starting… I always feel lazy to do one but the risks of not having one are bigger. Good luck!

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