My company is in the process of rolling out Active Directory enterprise wide, with office 365 syncronization, Lync, Exchange, and Outlook.

We currently have no AD (yet); there are 400+ users in 5 separate offices.

The quandary we are facing is whether we should initially deploy Windows Server 2012, or 2008R2.

Certain elements are afraid of unknown issues with 2012, and one of our contractors suggested that we use 2008 because it has a larger knowledge base.

I've done all my testing in 2012, and I know that either one will work for our purposes. It's a fairly simple deployment (2 DCs and 1 ADFS server).

We will also be adding WDS, WSUS, Sharepoint, and WebHelpDesk.

Is there any valid technical reason that we should not go with the latest available version, assuming this is a complete description of the environment, or any caveat with Windows Server 2012 that we should be aware of?

  • 4
    What do you mean by "We have no AD"? You've got 400+ users at 5 offices, on a "workgroup"?
    – Warren P
    Oct 29, 2012 at 20:43
  • 1
    That is correct, 400+ users in a workgroup. I was just hired on to improve the networks security, and AD is the first step. Its a SMB that has grown over the past couple years, and the infrastructure has not grown with it. On the bright side, we have a fairly powerful vSphere server, so I was able to build a full sandbox enviroment to test integration with out existing cloud services and servers.
    – Matt Bear
    Oct 29, 2012 at 21:45
  • The biggest irony is, we're buying server 2012 licenses, and using the downgrade option to run 2008r2, and we have all our users in office 365, and have to do an export from o365, import into AD, and then sync.
    – Matt Bear
    Oct 29, 2012 at 21:50
  • You can't buy 2008R2 licenses from MS anymore; you can only get them from vendors who have them "in stock" already. As you noted, there's no point as the downgrade rights are there.
    – Chris S
    Oct 30, 2012 at 1:09
  • 1
    The only reason it would make sense not to use the latest version is if you had something already deployed and integrated into AD that didn't play well with the latest version. As you don't have AD at all (!) this isn't an issue.
    – Rob Moir
    Oct 30, 2012 at 12:25

4 Answers 4


The only reason I can suggest for delaying a move to 2012, is that you have an existing domain architecture that won't cleanly upgrade. But since you have NO Active directory deploy yet, I take it that you're using the whole LAN in "workgroup" mode and without any domain at all, this is a trivially easy case to install Server 2012 on, and the new tools are the easiest tools yet, for creating a brand new ActiveDirectory Domain Controller and related infrastructure. If however, you mean you're still using Windows NT Server, pre-Active-Directory-domains, then I don't know if you're even going to get that all the way up to 2008 R2 in one go. You might want to update your question and specify what you mean by "having No AD" right now.

Get a book, either way you go, and learn about ActiveDirectory before you deploy it. I am running a mixed 2012/2008R2 domain server environment at our office, and I find that while I know the existing 2008R2 tools better than the 2012 tools, the 2012 tools are superior in every way, except for certain odd little tasks, and you can still access the old 2008R2 user interfaces if you want to, in 2012.

Both Windows Server 2008 R2 and 2012 are fantastic products. I see no reason not to deploy the latest version (Server 2012) in small LAN environments or for brand new ActiveDirectory deployments, and many technically advanced features in 2012, that are good reasons to prefer deploying 2012.

In large network environments with existing 2008 R2 infrastructure, obviously, there would be sensible reasons to deploy more 2008 R2 domain controllers, instead of moving only part of a huge 2008R2 network's servers up to 2012.

  • 1
    I found a few Dell server boxes that don't have drivers for their DELL PERC cards available yet for Windows Server 2012. THAT's another reason why someone might delay; Awaiting drivers for your hardware.
    – Warren P
    Nov 15, 2012 at 20:45
  • It seems all Dell hardware is nicely supported for Windows Server 2012 now.
    – Warren P
    Mar 12, 2013 at 13:38
  • You should be able to run the 2012 DCs still, and keep the domain at the 2008R2 functional level until you can clean up whatever mess is preventing the upgrade, if there was an existing domain. I believe the functionality is, as always, a strict superset of the previous version. Aug 14, 2013 at 1:37

The General Case: use $LATEST_VERSION unless you have a specific need not to.

You almost certainly fall into the general case, even more so since you lack "legacy" anything to hold you back.

It's true there could be unknown "issues" with 2012; but considering 2012 is mostly an incremental change to 2008R2, and the relatively extensive testing already done, I'm confident in considering it production ready (along with a large number of other users). You'll find a few talking-head websites that argue the days for waiting for SP1 before considering a Windows OS Production Ready are dead, and have been for sometime.

  • I tend to agree with you, however the powers that be are trying to be cautious, so we are going to move forward with 2008r2 with the plan to upgrade at some point in the future.
    – Matt Bear
    Oct 29, 2012 at 20:38
  • 3
    That makes very little sense, but you will be comforted to know that a 2008R2 to 2012 upgrade is relatively painless.
    – Warren P
    Oct 29, 2012 at 20:44

Speaking from the perspective of someone who has several times inherited "safe" versions I urge you to use the latest unless there is a real and unavoidable reason not to. While to some it might seem safer to use an old version on the basis that there should be no surprises, that's exactly what testing is for.

Quite simply, without a real reason to do otherwise, it makes no sense to install a version that is already 4 or 5 years old. Sure it might appear to make a little sense today but what about a few months from now, or a year or 2 down the track. Why create the extra work of upgrading later when there's no need to do so?

  • Exactly. I hate when I spend 3 days solving an issue on a W 2008 R2 server that would never have happend on WS 2012.
    – Warren P
    Nov 15, 2012 at 20:44
  • The systems I inherited are still running Server 2003 and I've even come across an NT 4 system within the last two years. :( Nov 15, 2012 at 21:10
  • Ouch. At least hopefully any remaining NT 4 or 3.5 systems are virtual machines kept around to run ancient binaries...
    – Warren P
    Nov 19, 2012 at 17:11

I would generally have said the latest version, but....

IMHO let other people Guinea pigs for the initial release! it's so radically different that there are bound to be some nasty surprises waiting to be ironed out in SP1. Wait for that and then you can consider an upgrade. Unless of course there is some needed feature in 2012 that you need right now.

  • my previous company had a policy of only using current version - 1 for that reason - let other take the fall, and we'll decide depending on the fallout.
    – SeanC
    Oct 29, 2012 at 21:08
  • 1
    We have a LoB vendor who believes this same crap (pardon my opinion slipping out); their software is constantly the one breaking and holding us back from upgrades. We have so many less problems with the OS and other software than we do with the "cautious" vendors.
    – Chris S
    Oct 30, 2012 at 1:08
  • I can't imagine the pain people went through when they decided to upgrade everyone to that OS that everyone would rather forget - Vista! Waiting for Windows 7 was wise.
    – hookenz
    Oct 30, 2012 at 2:49
  • I don't think it's totally necessary to wait till SP1, but since 2012 has only been out for a short time it's relatively unproven. Perhaps by the end of the year even if SP1 isn't out you'll have a good idea as to it's quality.
    – hookenz
    Oct 30, 2012 at 2:54
  • 2
    @ChrisS: At a small struggling software company, blaming everything else you can possibly blame for what in the end comes down to your own poor practices, and your own buggy code is standard operating procedure. I know because I've worked at several. I'm not blaming anybody, it's just a sign that there's a lot of stress on that vendor, probably due to a large backlog of bugs.
    – Warren P
    Dec 10, 2012 at 13:55

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