Posting on behalf of a non-profit I help out at. They currently have an on-premises Windows Server 2012 R2 Essentials install. They're close to hitting the 25 user limit. Upgrading to a Standard release of Windows Server is the only feasible option. Does anyone know if it will be possible to upgrade directly from Windows Server 2012 R2 Essentials to Windows Server 2016 Standard? Money is a major concern, so they're keen to avoid having to pay to upgrade twice (either 2012 Essentials -> 2016 Essentials -> 2016 Standard or 2012 Essentials -> 2012 Standard -> 2016 Standard).

I know that some well-meaning people are likely to suggest moving to a Linux server, but we've had to rule that out. I'm a Linux person and would ordinarily recommend it myself, but they need to be able to run some proprietary Windows only software, and they also need to be able to do some maintenance themselves. Linux has been considered quite extensively but it's not a viable option as I can't always be on hand to help and their other computers and experience are exclusively Windows.

Thanks in advance for any information. I've been unable to find anything online about this particular topic.

  • 3
    Possible duplicate of Can you help me with my software licensing issue? – longneck Jul 12 '16 at 20:09
  • Licensing questions are off-topic here. You're going to have to buy the license from a reseller somewhere, and they are best equipped to tell you what the licensing costs and paths will be. We do not have this information – longneck Jul 12 '16 at 20:10
  • Apologies, I wasn't aware of this policy. We're intending to buy direct from Microsoft to avoid the costs of using a middleman, and as far as I can tell, Microsoft don't answer licensing questions. I don't entirely trust a reseller to give an honest answer either, since they have a vested interest in selling extra licences. Still, I appreciate that it's a complicated issue and I understand why StackExchange is unwilling to accept questions on the topic. If only there was somewhere I could find an unbiased answer to these questions... – Kitserve Jul 15 '16 at 10:54

You can convert an Essentials license to a Windows Server Standard license. https://technet.microsoft.com/en-us/windowsserver/dn527667.aspx

You would then have 6+ years to upgrade that before support runs out.

Windows Server 2016 hasn't been RTM yet, so upgrading to 2012 R2 now certainly would not be considered a bad move. I'm not sure if you're big enough to qualify for Software Assurance, but that would guarantee you the right to upgrade to 2016 for free when that is released. If you don't qualify for SA, you should check with a reseller about downgrade rights with 2016, which could allow you to install 2012 R2 Standard first (while also upgrading from Essentials to Standard) and then upgrade to 2016 later.

Please note that Windows Server 2016 changes the licensing model: up until now, buying a Windows Server license generally covered you on a server with 2 physical CPU sockets. With 2016 you will be required to pay for a minimum of 8 CPU cores, or a minimum of 4 two-core license packs. Microsoft has already advertised the list price of 2016 Standard as $882. I'm not sure what am upgrade would cost with this change, but feel that this information might further push you towards 2012 R2 Standard for now.

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  • Unfortunately this is probably the most expensive option, that we're hoping to avoid, but I appreciate the input. The consensus here is if we have to pay the full cost for a Standard licence then it would be much better just to pay once for the 2016 edition. Your point about sockets vs cores was very helpful. – Kitserve Jul 15 '16 at 10:42

Extended support for 2012 doesn't end until 2023, so unless they need 2016 for something specifically you may want to opt with just upgrading from essentials to standard and sticking with 2012.


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  • Thanks, I'm aware of the ability to convert from 2012 Essentials to 2012 Standard. Given the costs involved I was hoping that we could move direct to 2016 Standard, on the assumption that it would cost about the same but would give us several years extra support. SturdyErde's answer suggests that I may have been wrong about that assumption. – Kitserve Jul 15 '16 at 10:45

I believe your original question was about "upgrading" - running on the same hardware. According to the docs, you can certainly do a clean install, but not an upgrade in-place between essentials and standard. So at some point, you are going to have to do a re-installation (and a possible upgrade if you go to 2012R2 standard first).

If they aren't using "tech soup" yet - they should, since that is (IMHO) the only wat to go for a non-profit.

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  • Thanks, this is very useful information. I hadn't realised that it's not possible to convert from Essentials to Standard without doing a clean install. I had a quick look at Tech Soup but the UK version isn't too clear about what's on offer, and things are further complicated by the fact that these guys are a non-profit, not a charity (this excludes them from Microsoft's charity offerings, for example). Still, one to remember for the future. Much appreciated! – Kitserve Oct 4 '16 at 19:48

A bit late to the party, but if I'm not mistaken, you could 1) Buy 2016 Standard with the required CALs. 2) Use your downgrade rights to convert 2012 R2 Essentials to 2012 R2 Standard. 3) Upgrade to 2016 Standard at your leisure. (Confirm that the type of license you purchase includes downgrade rights.)

Re. non-profit purchasing, I'm only familiar with U.S. options, where Tech Soup is the cheapest (basically administering Microsoft donations), and if that's not available, you would hopefully qualify for non-profit licensing, which MS will only sell you through a short list of authorized distributors.

Start here: https://www.microsoft.com/en-us/philanthropies/product-donations/

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  • Much appreciated! I'm fairly certain that in the UK, Microsoft only offer discounts for organisations with legal charity status. Not-for-profits, social enterprises, and other NGOs/ethical businesses are not included. – Kitserve Aug 1 '17 at 14:00
  • Following through the link I posted takes me to microsoft.com/en-us/philanthropies/product-donations/…, which says UK tax-exempt organizations also qualify. "Organizations must be nonprofit or non-governmental organizations with recognized charitable status in their respective location: England and Wales, registered with the UK Charity Commission and/or registered with HM Revenue & Customs (HMRC) as tax exempt;..." – Mark Berry Aug 2 '17 at 15:14
  • I appreciate the input, but not-for-profit companies are not usually tax exempt. That's certainly the case for this particular organisation. – Kitserve Aug 20 '17 at 19:14

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