How to Purchase License of MS Server 2012 Standard to load on VMWare

I currently have a Dell PowerEdge 2950 with VMWare ESXi 5.5.0, 1623387, 2 Intel Xeon CPU E5440, VMware vSphere 5 Hypervisor- Licensed for 2 Physical CPUs (unlimited cores per CPU), 16GB RAM with 2 1TB drive in RAID 1. I have 2 WIN7 VMs installed on the machine. I need to load a new VM running either Server 2008, Server 2012 or Server 2016. These are requirements of the software that needs to be loaded to the machine. When going through the wizard on vSphere client to add new machine, under Guest Operating System>Windows, the latest OS this version of VMWare is capable of loading is MS Server 2012. I have spoken to my 2 main vendors for MS Licensing (CDW & Tech Data) and they have both told me the oldest downgrade version the can sell me is Server 2012 R2. Can anybody please direct me to my best course of action. I know I have multiple options but am not sure which to take. Any help would be greatly appreciated. End user does not want to have to purchase new hardware to install software on if possible.
fenski4435IT ConsultantAsked:
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Andrew Hancock (VMware vExpert / EE Fellow)VMware and Virtualization ConsultantCommented:
ESXi 5.5 U3 supports Windows Server 2012, 2012 R2 and 2016, just select Windows Server 2012, and install as normal.

Please note ESXi 5.5 is now end of life and not supported.

Your current version of ESXi 5.5 is U1, you will need to upgrade to U3 for ALL of those operating systems.

So purchase 2012 R2, 2016 and install!!!

BUT your biggest issue is U1 to U3 upgrade for ESXi, do you have support ?
fenski4435IT ConsultantAuthor Commented:
We do not have support and I am not, by any means, a VMWare expert. Hence the rather simple question initially posed. Thanks for the information. Is there documentation to upgrade ESXi from U1 to U3? What are the risks?
Andrew Hancock (VMware vExpert / EE Fellow)VMware and Virtualization ConsultantCommented:
No problems on upgrading, I can guide you.

The upgrade is covered in my EE Article

HOW TO: Upgrade VMware ESXi 5.5 to ESXi 6.0 in 5 easy steps

BUT, the issue is having access to the U3 upgrade, which without you cannot run the Microsoft OS.

As for risks....I don't think there any more risks, than your current risks.

1. No support.
2. ESXi 5.5 end of life.
3. Dell Server end of life.

I can guide you through the U1 to U3 upgrade, if the software is available.
fenski4435IT ConsultantAuthor Commented:
Thanks for the information. I believe we have the company I contract for is a VMWare partner so support may not be an issue. Unfortunately, the owner of the company is currently hospitalized for a couple of days so I will not be able to find out until end of week. I need a few points of clarification:

1. Can we load Server 2012 Standard on U1? Is this wise?
    - Do you know if you can even purchase Server 2012 license anymore? We are having trouble doing so.
2. Your statement "BUT your biggest issue is U1 to U3 upgrade for ESXi, do you have support ?" relates to the ability to acquire the U3 upgrade. Correct?
3. I assume that with the existing VMs backed up and powered off and with the server in maintenance mode, there is not risk to those machines.
4. Can you use OEM software to load to VMWare?
5. Is MS licensing different for VMWare than for Physical Server?

I greatly appreciate the information you have provided. I am going to need to spend some time trying to find out about our partnership status with VMWare as well as a few other things. I will get back to you when I have more information. Thanks again. You have been extremely insightful.
Andrew Hancock (VMware vExpert / EE Fellow)VMware and Virtualization ConsultantCommented:
1. It's not supported, and may not function. Hence the suggestion to upgrade to U3.

2. Correct.

3. Correct.

4. Please explain.

5. No. Every purchase of Windows Standard, entitles you to run 2 VMs.

But Microsoft now licenses VMs by Cores.

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