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We have a server running SBS 2011 Standard with an eval. license which we had originally planned on purchasing, however, we now have decided we want to use Essentials instead. Will this switch be as simple as popping in the CD and saying "upgrade" or will it require using migration tools to make sure all of our settings are still applied?

We are not using any of the features that would be absent in Essentials, and as far as the Windows Server features, it is our DC, AD server, and file share server. The other third party services we use (e.g. Subversion, license servers, etc.) are all easily reconfigurable if need be.

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We started on SBS many moons ago (4.0), and I'll give you the advice I wish someone had given us back then: just spring for a standard sever (2008 R2) license and CALs. Over the years, SBS has gone from a full featured (DC, Exchange, SQL, ISA) product to being a 'Celeron' style (SBS Esssentials) alternative to the standard Windows Server. Being locked into it creates non-trivial barriers from both a licensing and a technical standpoint to migrating to something else. Neither of these is at all insurmountable, but it takes money and effort that could be better spent on other things.

Sorry for the rant, but like I said, I wish someone had given me that advice in, oh, say, 1998.

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We've already bought the license, lol, and our last Windows Server was around since 2000, so either way migrating to a new box won't be for a while, and it will likely have to be a complete migration anyways. Plus, we are apretty small business, spending ~500 on a license makes much more sense than spending a few thousand in CALs – Alexander Miles May 20 '11 at 17:38
How can say it's a "Celeron" version of Windows Standard when it comes with Exchange and Remote Web Workplace among other features you can't get or have to pay more for with a standard license. – gravyface May 20 '11 at 17:41
I understand, that was our logic too -- my hope was that you hadn't bought the license yet, but if you have and you know you'll remain under the 25-user no-cal limit then carry on and good luck. – nedm May 20 '11 at 17:59
@gravyface, I was referring to essentials - no Exchange. – nedm May 20 '11 at 18:00
Yeah, we're not about to be using Exchange any time soon – Alexander Miles May 20 '11 at 22:57
up vote 0 down vote accepted

Well apparently you can't just "Upgrade" as if it were a desktop install, so I performed a server migration to a new VM and, for the most part, it was pretty painless.

I followed this guide to help me through the process, most of the steps were the same with minor transpositions. The only issue I had is that at the end of the migration process, the Migration Mode flag was never set to false and I lost access to the Dashboard, though I think it may be because I did not give ample time for the source GPOs to replicate to the destination server before running DCPROMO on the source.

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