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OEM license change possible on a server?

Hello All,

I am need of doing some server virtualizing... However my problem is that most of my physical servers are OEM licenses and i hear the Physical to Virtual tools will fail on OEM licensed servers? My question is can i just buy non OEM licenses and apply them to the server so that they no longer show OEM? I assume i can just go into the activate license option on the servers and change the key and apply?

Anyone have any insight if I can do that or not? I have 5 servers that are a mix of 2008r2 and 2012r2 that i need to virtualize and it would my much quick to use the tool to convert and image to my new AHV solution rather than build a new server and migrate each server 1 by 1.

Any insight is greatly appreciated.
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Tom Cieslik
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No problem
Use Disk2VHD software and it will create VHDX file
I have virtualized over 30 OEM Dell server in the past - all success.

I've never heard that OEM is a problem, Only problem you can have is with Domain controller virtualization because in some cases is software can destroy metadata but If you need to do it, just disable DNS service and DHCP service and all will be fine. I did this twice with DC
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Interesting... So OEM licensed servers wont break once brought online as a VM? The idea i guess for us is to use the VM converter to make the VM from the physical server... And then Nutanix converts the VM image to an AHV image...

However I have never done this and Arrow which is the company that will help with the P 2 V says OEM breaks once converted.
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Could i then just apply a new OEM license at that point?
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OK so that made it even more confusing... Will or wont the p2v's OEM servers come up/run and work on the AHV solution?
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OK so it will work... Activation may break but then i could just put in another OEM license that has not been used in the past correct?
Activation may break but then i could just put in another OEM license that has not been used in the past correct?

Probably not, since that OEM license is still going to be tied to a particular physical host. I should have mentioned this in my previous post, but in a Nutanix environment (or really any clustered environment), volume licensing is preferable to OEM licensing, since the volume licenses aren't tied to a particular host. Volume-licensed VMs will stay activated no matter what host they're on.
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A new OEM license that has not been used or bound to a host will not work on a new VM?
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Its not about being cheap... Just happen to have these already purchased...  If i get non OEM licenses can i apply them to the servers i have that are OEM now so that they are not OEM when i do the p2v? Will that work?
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Ok... So just to make sure i get it right...

Buy NON OEM licenses... Go to current OEM servers and re-enter the KEY and activate.... This will now make the license acceptable for me to p2v....

Placing the key and doing a new activation shouldn't break anything correct? Also may sound like a dumb question but where can i buy non OEM licenses? I have a couple 2008r2 and a couple 2012r2... Do i just buy the 2016 standard keys and those will work? Do I have to register them with MS and do the whole open license thing or is there a way to purchase these online?
The installed OEM licensed operating system can't be rekeyed as I understand things. It's bound to the physical hardware. Only the guest OSEs can be moved if the physical box is running a hypervisor such as Hyper-V or VMware.
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Seems like i am getting a ton of mixed answer... Some say p2v on OEM works fine... Some say it doesnt... Some say i can update the OEM key to Open and some say i cannot... Think i am more confused now then i was before i got here lol.
It will work but according to Microsoft OEM agreement it will NOT be legal.  

So again,,, technically it's possible and it will work,,,legally.....you must decide.
Please read Eric Siron's post in the Technet Forums here.

What he says is defacto correct. OEM physical OS install cannot be moved but the guests licensed via the host can.
Okay P2V process will work that is not the issue.

But it may break the Activation!

And that then requires an OS repair using a new retail key if you used Retail CD-ROM to repair
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Thanks Andrew...

To get around the repair part... Can i somehow change the key on the OS before the p2v happens? Can i just log into the server, hit the activation button and put in a new NON OEM key and go forward? Or will that break something also?
You cannot buy anything less than Server 2019 directly from Microsoft and you will need to buy Software Assurance in order to get downlevel keys i.e. Server 2008R2 -> Server 2016.

If you feel lucky and don't get audited then the OEM versions will work. If you do get audited then you are in a world of hurt.  If you lose a system administrator and they report your company to the SPA then you are in for even more world of hurt.
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Hello David,

Again... I have no issues paying for whatever is needed... I just do not want to rebuild any servers or have something break when doing the p2v... My question is can I somehow change the OEM license so that I dont have to worry when i do the P2v?
So if you have no problem to pay, just do upgrade then,, on virtual machine run DISM command

Dism /online /Set-Edition:ServerStandard /AcceptEula /ProductKey:xxxx-NCCV3-xxxx-FXW9B-xxxx

(You must put your edition name) If is Standard, then Standard,,, if  Datacenter then ServerDatacenter,,, etc depends what kind of new Key you going to use.

This command will replace your OEM key by your new VL or Retail,,, then you will be able to activate new key on Virtual Machine.
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When you say do upgrade to do you mean just updating the license key on the physical server before I do the p2v? Sorry for the dumb questions I just want to be 100% sure I am understanding...

When you say on the virtual machine it confuses me sorry... So dont do anything to the current physical OEM server... Go ahead and do the P2V and bring up the VM and then apply the new license key? Is that what you are saying i can do?
Doesn't matter before P2V or afterward.
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Andrew... So I should change the license key from OEM to non OEM prior to the p2v correct?
Firstly P2V is just a process which will complete. (or should complete!)

but you may want to read this, I wrote.

HOW TO: FAQ VMware P2V Troubleshooting

Your issue is OEM is not supposed to be MOVED from Physical to Virtual hardware, it could be a breach of the licensing based on where you are located in the World.

Your INSTALLATION (media) is OEM.

and this then becomes difficult to override this!

Basically, you've got to try it... but do not be surprised if you waste your time.

It may be better to transfer the services to a new server.
OK, to cut this discussion I have did this test for you to proof that there is NO problem at all.
It is not legal so to use it You must convert license using DISM command I've provided before but IT WILL WORK !!!

I've converted to Virtual my Windows 7 Pro OEM from Dell computer.

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Thankyou everyone for you responses.... I guess we will try it and if it works great and we will change the license key, if not then we will build them 1 at a time over again... Just have to try it and see I guess. Does anyone have any good outside vendors that they know of that will help with this? If so ill call them and get some quotes... I have 1 other question.... I am told that buying 2019 licenses with downgrades rights is the way to go which is what i will do... However I am told that each license i buy i could actually use for 2 servers on my hypervised solution... Is this correct? So essentially each license I buy I can use on 2 servers so long as they are on my Nutanix AHV solution? I have 7 servers in total that I will be moving over to my AHV solution and if that is the case i can suffice with getting 4 2019 licenses. Appreciate the responses.
Correct, 1 Windows Server Standard includes to Virtual Machine licenses, and Windows license are now based on Cores in the Host!

But, a cost effective solution - Datacentre license includes unlimited.
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Hello Andrew.... Any way you can elaborate on that? Are you saying if I buy a Datacenter license I could have unlimitted licensed servers on my AHV?
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Also does 1 datacenter license allow downgrade rights to many versions or will it have to all the the same version? Meaning if i need 3 2008 r2, 3 2012r2 and 3 2016 all on my AHV will 1 2019 datacenter license suffice?

Damn.... Maybe this wont work... Just noticed you said 16 cores... Is that 16 cores max on each server using the license or 16 cores MAX on the HOST that is supplying that VMs? If so why would people go this route being maxed at 16 cores? My AHV 3 node is 16 cores each which total 48 cores... In this case I would have to buy 3 of these? Which would equate to about 15k?
Hello Andrew.... Any way you can elaborate on that? Are you saying if I buy a Datacenter license I could have unlimitted licensed servers on my AHV?

Yes, as many as you have resources.

So you may want to calculate the cost or standard versus datacentre, because there is a break even point of the numbers using standard.

see here

https://www.microsoft.com/en-gb/cloud-platform/windows-server-pricing
How many processors, and how many cores do you have you need to license in the host ?
7 or less virtual machines use standard as standard is about 1/8th the price of datacenter.
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Its 6 total processors... 8 cores per proc.... Each node is 2 procs and 16 cores.... Meaning the entire 3 node solution is 48 cores. In this case i would need 3 data center licenses? Seems way over priced for the total of 7 servers i want to move to it. That would equate out to be like 15k for the 7 server licenses?
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Thanks David.... Now will 4 standard licenses suffice for the 7 servers since they are VMs? Or is the info i am told not accurate that each standard license will work on 2 VMs?
How many CPUs in the Host ? 2 ?

How many cores per CPU in the Host ? 16 ?
So per Node....(host)

1 x Windows Server® 2019 Standard (16 core)       
1 x Windows Server® 2019 Standard Additional License APOS (16 core)      

this licenses the 32 cores.

96 additional cores need to be licensed

6 x Windows Server® 2016 Standard Additional License APOS

So to license a NODE (single HOST) for 7 VMs

You need to purchase the following

1 x Windows Server® 2019 Standard (16 core)       
1 x Windows Server® 2019 Standard Additional License APOS (16 core)      
6 x Windows Server® 2019 Standard Additional License APOS

(in fact you can have 8 VMs, as licenses are in twos!)

2 VMs are included in the Standard Base License once all physical cores are properly licensed.
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its 3 nodes... So i assume each node is a host? Each node is 2 cpu's and total 16 cores.

I think my best bet is just buying standard licenses for each server i want to move over to the solution... My question now is do i buy a license for each server or since they are going from P2V do I only need 4 licenses since each standard license will work for 2 VM servers?
Yes, 3 seperate hosts. (nodes).

Licensing is now based on Cores.

if you need to license 7 VMs per Node

You need to purchase the following for each Node (host)

1 x Windows Server® 2019 Standard (16 core)      
1 x Windows Server® 2019 Standard Additional License APOS (16 core)      
6 x Windows Server® 2019 Standard Additional License APOS
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How does that work with the VM's? its 7 VM's in total over the 3 nodes.... only a couple VM's run on each node at a time... The other node is just there for failover.

Node 1 = 2 VM's
Node 2 = 2 VM's
Node 3 = 3 VM's.
are you going to lock the VMs to those nodes ?

if 7 VMs could run on a node, all cores need to be licensed.
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I have 7 VM's...... 3 nodes in total... Are you saying i need 21 VM licenses even thought only 7 are turned on at any given time? I thought the entire reason for non OEM is for transfer in case an outage and the license wouldn't be bound to that physical hardware? That would literally defeat the purpose of going a virtual route and make it non cost affective solution.
To expand upon the previous comment.  If the vm's COULD run even for 1 second on a node then all cores need to be licensed. i.e. failover, backup with testing i.e. Veeam SureBackup.
Do these VMs "move" around the cluster ?

is it possible that 7 VMs could be running on a single node ?

Then yes.... what you need to purchase is

3 x Windows Server® 2019 Standard (16 core)      
3 x Windows Server® 2019 Standard Additional License APOS (16 core)      
18 x Windows Server® 2019 Standard Additional License APOS
(12 x if 5 VMs)
This then licenses you for your cluster of 3 nodes, and 7 VMs.

All cores must be licensed.

Do you only have 7 VMs total, no other VMs ?

(original post stated 5 VMs which changes the numbers a little)
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OK so i called and made sure I got this correct and thank you all for letting me know what i need.

I have 7 total VMs.

I am told that the each VM would be locked to only 2 nodes of the 3 which should help in licensing.... So even though its 3 nodes each VM server  is locked to only 2.

I just want to make sure I have this correct so I know what to buy and be in compliance.



And this... Is this just 24 2019 standard licenses? I know you have a breakdown below but isnt this just 24 standard licenses if i were to buy?
3 x Windows Server® 2019 Standard (16 core)      
3 x Windows Server® 2019 Standard Additional License APOS (16 core)      
18 x Windows Server® 2019 Standard Additional License APOS
(12 x if 5 VMs)
Okay, so if the VM does not move to the third. (if you had an audit, you would have to prove and document this is the case!)

Then you can just assume two hosts in the cluster.

2 x Windows Server® 2019 Standard (16 core)      
2 x Windows Server® 2019 Standard Additional License APOS (16 core)      
12 x Windows Server® 2019 Standard Additional License APOS

The above is what you need to purchase.

And this... Is this just 24 2019 standard licenses? I know you have a breakdown below but isnt this just 24 standard licenses if i were to buy?

No, the above is what you need to purchase. A Standard License and then the additional licenses.
Question about cores and licenses should be moved to separate question, since original question was if is possible to transfer OEM Windows server to  VM.

I think this was already answered.
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Thanks... I called MS and they told me a completely diff answer to my license question... As long as I get datacenter it will have license mobility and will allow the product to be brought up on another node and will not need to purchase separate license for each node... Glad I called because that just saved me 15k+. I could either buy 7 standard licenses with SA and license mobility to do this or just get datacenter which is about the same cost....
So a single Microsoft WIndows Server 2019 Datacenter, covers all your license requirements?
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Windows Server 2019 Datacenter - 48 Core License
Unlimited Virtual Machines.
Includes licensing for 2019, 2016, 2012 R2, and 2008 R2 Datacenter.
That is only if you have a current or new Software Assurance package
So,, If I have Host with Windows 2019 Datacenter, it is possible to install "unlimited" amount Windows 2019 Standard as clients (VM's), or all of them must be Datacenter edition ?
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From what I am told by trustedtech you can  install unlimitted versions of Server with data center edition as long as you are under the core count of the datacenter license. Also what was told to me was I did NOT need SA.
Unless you already own the previous Windows Server versions you will need Software Assurance to be able to install downgrade versions. Without software Assurance each version of Windows Server has its own costs. Software assurance gives you the ability to get the VL versions of the previous windows server versions and use them at no additional charge.
So,, again.. If I'll purchase Windows 2019 Datacenter and Build VM Hyper-V Host,,, ca I use it to install VM clinets ? same license key ?
I don;t understand how Microsoft will allow me to activate same Key multiple times ?
They do.
Activation and Licensing are not the same

You might want to try Automatic Virtual Machine Activation https://docs.microsoft.com/en-us/windows-server/get-started-19/vm-activation-19
Note that AVMA only activates server versions back to 2012 R2. (Of course, if you need to run versions older than that, you've got issues that go beyond licensing and activation.)
And AVMA doesn't activate VM's running on a non Windows host like VMWare...
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