Perpetual Windows Server Licensing

RTSS01 41 Reputation points
2022-03-03T16:08:04.2+00:00

I'm trying to set up a lab/testing environment for pen testing and ethical hacking.
I want to have Backup/Golden VMs that I can clone and later destroy, whenever I run into a particular Windows Server version in the wild. The purpose is to test exploits in a controlled environment prior to running them on client's production boxes.

I know I'm going to run into old versions of Server long after MS stops supporting them, even 10 or 20 years down the road. In recent engagements I've run into XP, Server 2K3, and Server 2K8.

I don't want to use eval/trial versions as that would require installation and setup over and over again through the years. I am not a CSP to have access to that type of licensing. The Partner Program doesn't seem to offer access to any form of perpetual or ongoing licensing, and only offers current versions.

I've reached out to a number of vendors and I'm getting conflicting information. Copies of Windows Server are not exactly cheap, especially some of the newer versions. I wondered if anyone here could give me something a little more authoritative to make sure I'm going about this in the proper way.

If I purchase retail, boxed versions of Windows Server, is that licensing perpetual and transferrable? Can I move my Backup/Golden VMs to another server when my current one dies or becomes obsolete? Is there even an option to do what I'm trying to do?
Searching online has been confusing at best and MS Support was basically useless.
Any direction would be appreciated.

Windows for business | Windows Server | User experience | Other
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Accepted answer
  1. Anonymous
    2022-03-03T16:30:15.493+00:00

    Sounds like you may be looking for a VS subscription.
    https://visualstudio.microsoft.com/subscriptions/#software-and-downloads?cat=visual-studio-enterprise-subscription-with-github-enterprise

    --please don't forget to upvote and Accept as answer if the reply is helpful--

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4 additional answers

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  1. Anonymous
    2022-03-03T17:04:26.97+00:00

    This is interesting. I guess it's the successor to MSDN?

    Yes, that's correct.

    can answer my question directly about boxed versions

    You can only buy the current version from microsoft so just be careful as to what you're buying via third party.

    --please don't forget to upvote and Accept as answer if the reply is helpful--

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  2. RTSS01 41 Reputation points
    2022-03-03T17:01:11.747+00:00

    @Anonymous
    This is interesting. I guess it's the successor to MSDN?
    Not sure I want to be beholden to paying Microsoft a monthly fee in perpetuity to keep my lab environment running. Some quick, back of the napkin math indicates it'll be just as expensive and maybe more expensive to do it this way in the long run. Though it would give me a far greater range of software to use in testing.
    I will definitely dig into this.

    I'm going to leave this out there for a bit to see if someone can answer my question directly about boxed versions. If no one else has something further, yours might be the best answer.

    Thanks

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  3. RTSS01 41 Reputation points
    2022-03-03T22:08:57.9+00:00

    I am not a lawyer, I'm certainly not the lawyer of anyone reading this. But I'm comfortable that licensing of boxed versions are transferrable to newer/replacement hardware based on the following parts of the Microsoft License Terms found here: https://www.microsoft.com/en-us/useterms/

    Windows 10:
    https://www.microsoft.com/en-us/Useterms/Retail/Windows/10/Useterms_Retail_Windows_10_English.htm
    4b. Stand-alone software. If you acquired the software as stand-alone software (and also if you upgraded from software you acquired as stand-alone software), you may transfer the software to another device that belongs to you. You may also transfer the software to a device owned by someone else if (i) you are the first licensed user of the software and (ii) the new user agrees to the terms of this agreement. You may use the backup copy we allow you to make or the media that the software came on to transfer the software. Every time you transfer the software to a new device, you must remove the software from the prior device. You may not transfer the software to share licenses between devices.

    Windows 11:
    https://www.microsoft.com/en-us/UseTerms/Retail/Windows/11/UseTerms_Retail_Windows_11_English.htm
    b. Stand-alone software. If you acquired the software as stand-alone software (and also if you upgraded from software you acquired as stand-alone software), you may transfer the software to another device that belongs to you. You may also transfer the software to a device owned by someone else if (i) you are the first licensed user of the software and (ii) the new user agrees to the terms of this agreement. You may use the backup copy we allow you to make or the media that the software came on to transfer the software. Every time you transfer the software to a new device, you must remove the software from the prior device. You may not transfer the software to share licenses between devices.

    Windows Server 2012:
    http://download.microsoft.com/Documents/UseTerms/Windows%20Server_2012%20Datacenter_English_97974250-7a55-4236-bde8-546f0cec9c85.pdf
    2c. Assigning the Required Number of Licenses to the Server.
    · Initial Assignment. After you determine the number of software licenses you need for a
    server, you must assign that number of software licenses to that server. That server is the
    licensed server for all of those licenses. You may not assign the same license to more than
    one server. A hardware partition or blade is considered to be a separate server.
    · Reassignment. You may reassign a software license, but not on a short-term basis (i.e.,
    not within 90 days of the last assignment). You may reassign a software license sooner if you
    retire the licensed server due to permanent hardware failure. If you reassign a license, the
    server to which you reassign the license becomes the new licensed server for that license.

    Windows Server 2016:
    https://www.microsoft.com/en-us/UseTerms/Retail/WindowsServer2016/DatacenterAndStandard/UseTerms_Retail_WindowsServer2016_DatacenterAndStandard_English.htm
    2c. Assigning the Required Number of Licenses to the Server

    · Initial Assignment. After you determine the number of core licenses you need for a server, you must assign that number of core licenses to that server. That server is the licensed server for all of those licenses. You may not assign the same core licenses to more than one server. A hardware partition or blade is considered to be a separate server.

    · Reassignment. You may reassign core licenses, but not within 90 days of the last assignment. You may reassign core licenses sooner if you retire the licensed server due to permanent hardware failure. If you reassign core licenses, the server to which you reassign the licenses becomes the new licensed server for those core licenses. You may need additional core licenses to cover all of the physical cores in the new server.

    Windows Server 2019:
    https://www.microsoft.com/en-us/UseTerms/Retail/WindowsServer2019/DatacenterAndStandard/Useterms_Retail_WindowsServer2019_DatacenterAndStandard_English.htm
    C ii. Microsoft. If you obtained the software from Microsoft ****(not via a manufacturer or installer)****:

    (a)Initial Assignment. After you determine the number of core licenses you need for a server, you must assign that number of core licenses to that server. That server is the licensed server for all of those licenses. You may not assign the same core licenses to more than one server at the same time.

    (b) Reassignment. You may reassign core licenses, but not within 90 days of the last assignment. You may reassign core licenses sooner if you retire the licensed server due to permanent hardware failure. If you reassign core licenses, the server to which you reassign the licenses becomes the new licensed server for those core licenses. You may need additional core licenses to cover all of the physical cores in the new server.

    Windows Server 2022:
    https://www.microsoft.com/en-us/UseTerms/Retail/WindowsServer2022/DatacenterAndStandard/UseTerms_Retail_WindowsServer2022_DatacenterAndStandard_English.htm
    C ii. Microsoft. If you obtained the software from Microsoft ****(not via a manufacturer or installer)****:

                                            (a)             Initial Assignment. After you determine the number of core licenses you need for a server, you must assign that number of core licenses to that server. That server is the licensed server for all of those licenses. You may not assign the same core licenses to more than one server at the same time.
    
    
    
                                           (b)             Reassignment. You may reassign core licenses, but not within 90 days of the last assignment. You may reassign core licenses sooner if you retire the licensed server due to permanent hardware failure. If you reassign core licenses, the server to which you reassign the licenses becomes the new licensed server for those core licenses. You may need additional core licenses to cover all of the physical cores in the new server.
    
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  4. RTSS01 41 Reputation points
    2022-03-03T22:11:13.523+00:00

    If one of the moderators can fix the misspelling in the title, that might help someone searching this topic in the future.

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