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Which version of Windows server to buy?

Our current only one server is 2008 R2 Standard. While we are buying a second server, I'm soliciting your suggestion about which version to go. We are not going to do virtualization. Should we simply go for 2008 R2 or move onto 2012 R2? Does 2012 R2 automatically come with a downgrade rights to 2012 and 2008 R2?
Please help.
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Distinguished Expert 2018
I don't ever think it is a good idea to intentionally buy older unless necessary. It is n unnecessary shortening of the lifespan of the purchase.

So buy the newest version that the workload currently supports (which will vary by hardware and application vendor, hence the "workload" caveat. As far as downgrade rights, that depends on how you buy and the specific agreement. Most VL purchases offer some downgrade rights. But some negotiated EA agreements don't, and OEM is always tricky, as the license may allow it, but leaves it up to the OEM to provide media and keys, which OEMs are allowed to decline to.
Lee W, MVPTechnology and Business Process Advisor
Most Valuable Expert 2013
Virtualization is not a new technology.  It's 2015.  It was included in Windows server 7 years ago.  And has been heavily used and supported with VMWare for over a decade.  While there CAN be instances that are not virtualization compatible, it's rare in my experience and you're shooting yourself in the foot considering that MS now provides MULTIPLE copies of Windows server even with Server 2012 Standard so long as you virtualize.  I strongly recommend you review your technological requirements and implement virtualization if they allow.  If your issue is skillset, then I will repeat that Virtualization is not new and you need to update your skills to include an understanding of the benefits and advantages (as well as disadvantages) offered by virtualizing.

That said, I agree with the sentiment as I understand it expressed by Cliff.  You really want to purchase Server 2012 Standard.  And for the flexibility of the license as well as included rights and access to prior media and keys, you want to obtain a Volume License version.  Odds are if you're small, you'll be going with a Open Business license which includes downgrade rights, media, and keys.  If you MUST use 2008 R2, it's easily obtained and installed buying the 2012 License.
Maheshwar RSoftware Developer
Buy the 2012 R2 Server , which then can be downloaded to sever 2008 if needed, but better buy the 2012 R2 server as the life cycle is more
Is cost a consideration?

For some situations the Server 2012 Essentials edition may be a more cost effective choice, especially where you've stated you don't expect to do virtualization. You just have to be aware of its limitations.

If you purchase and install 2012 Standard edition, you'll need to get 2012 CALs to go with it.