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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.

Kitserve
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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.

https://support.microsoft.com/en-us/lifecycle/search?sort=PN&alpha=Windows%20Server%202012%20R2&Filter=FilterNO

lucky255
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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.

Sam Erde
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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.

Scott
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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/

Mark Berry
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