Windows 10 Upgrade - Small Office Domain - Win 7 Pro OEM Licenses (~100 Machines)



  • So we are pushing forward with our free upgrade to Windows 10 in our office. All machines are domain joined and have Windows 7 Pro OEM licenses. We would like to upgrade each machine instead of pushing a new image to limit the impact to our users. Hardware is all compatible (we will replace/upgrade if we run into one we missed). We've tested all applications with Windows 10 and have manually upgraded a few machines for testing / feedback. We have our Windows 10 GPO configured to fix all of the issues we have encountered due to our environment.

    Unfortunately since we are a small company we do not have any subscriptions to Microsoft's nicer products (SCCM, etc), but I could maybe swing a purchase if I can demonstrate cost savings.

    Regarding GPO, this is the first time I have had to deal with transitioning GPO settings to new Windows templates. What is the best procedure for ensuring everything that needs to be moved to the new templates is done properly?

    • How did everyone here do it in their small business environment?
    • Do you think I could just shudder let the windows updates loose via our WSUS server on a controlled basis? shudder (I feel dirty even typing that)
    • How much hands on per machine would be required and what level of technical skill would it need if we did allow upgrade through Windows Update? shudder
    • Did you run into any strange problems?
    • Is there anything that I should be aware of or plan for that might not be obvious?
    • GPO Update Recommendations?

    Thanks in advance for any tips provided. I appreciate all the help that can be provided



  • I didn't think businesses were included with the free upgrade.

    Was I wrong or aren't businesses still expected to purchase Windows 10?



  • I thought all Home and Pro versions were covered, the only ones that technically aren't covered are the Enterprise editions. Those should be covered by the SA on their license agreement though, assuming it hasn't expired.



  • I thought you needed to have SA for the upgrade. You can always check your VLSC account to see what you have. Also, I don't think Windows 10 is any exception to performing clean installs instead of in-place upgrades. I have already seen really strange issues from people doing the in-place upgrades.



  • I would also like to add that you don't need SCCM to deploy images that are pre-configured and automated. Look into MDT with WDS PXE booting. I have it setup and image all PCs. It is included in Windows server licensing.

    I haven't set this part up, but you can even have it pull the user profile settings from an older system first then apply it to a new one.



  • @wrx7m that sounds really good, but would it work with my licensing? Wouldnt I need VL for that?



  • I am currently in the middle of my own 110 unit upgrade.

    I do have SA on a few Windows 10 machines which grants me the permissions to do imaging, OEM licenes themselves do not.

    I created an image the way I like it, I backup a few things from the the PC, I run gatherOSState.exe from the install media to create my upgrade rights file save it to a device, then install Windows 10 OEM, put the gatherOSState output file on the machine, ensure it activates, then wipe and load my image.

    All said it takes me about 2 hours per machine.



  • @Dashrender I was speaking to Microsoft about this situation late last year, and they hinted at purchasing 1 Win10 VL and using that. Im really doubtful due to licensing issues. Do you think it would work?



  • @Brains said in Windows 10 Upgrade - Small Office Domain - Win 7 Proe OEM Licenses (~100 Machines):

    @Dashrender I was speaking to Microsoft about this situation late last year, and they hinted at purchasing 1 Win10 VL and using that. Im really doubtful due to licensing issues. Do you think it would work?

    Absolutely it works.

    To get into VL licensing you have to buy five licenses, it doesn't have to be five Windows Software Assurance, just five total. The cheapest will probably be - one Windows Desktop upgrade with SA and 4 CAL licenses.

    With that single SA you'll have access to the media so that you can create images for that single version. But that alone doesn't get you what you need.

    The upgrade process is a PITA. You have Win 7 Pro OEM licenses today. You have to upgrade those licenses first. There are two ways to do this.

    1. do a normal upgrade - this will go through the traditional upgrade process and register your machines with MS as having a valid Windows 10 Pro license.
    2. extract gatherOSState.exe from the install media, copy it to the desktop, run it, and save the GenuineTicket.XML file that it generates. Now format the machine and install Windows 10 from scratch, while completely disconnected from the internet. Before putting the computer on the internet, put the GenuieTicket.XML file in C:\ProgramData\Microsoft\Windows\ClipSVC\ directory, and reboot, while rebooting, put the computer on the internet.

    Log in and check the activation status. Assuming it activates, move to the next phase. If it does not activate, try entering the Windows 7 key from the sticker on the computer. If it activates, move to the next phase, if not, post for more help.

    Next Phase - now, assuming you did a fresh install, and you have an image to deploy, boot from your image deployment tool of choice and import your image. Finish setup post image, done.

    This process is highly glossed over, and as I mentioned takes me around two hours. I probably spend 30 hours building my image, trial and error.

    I use Clonezilla for my imaging solution.

    When building your image, assuming Clonezilla or FOG, look into Audit Mode for Windows 10 while building your image.



  • @Dashrender

    Have you tried your method without upgrading first?

    I have done them all thus far using install media, and it used to require that, but now no longer does. It just activates.



  • now you said you didn't want to disrupt your users that much - You can skip all what I wrote above and just install the upgrade. I hear it works pretty well most of time.

    Doing this preserves all of your user's data (though you should absolutely have a backup before considering this) along with their browser settings, etc, etc, etc,etc.

    but as @wrx7m mentioned - I've seen strange things with upgrades and personally don't like them. I know that @scottalanmiller had major issues after his laptop was upgraded to Win 10, not sure he ever "refreshed" it to a clean install state or not? I think he bailed on it and went Linux instead.



  • @BRRABill said in Windows 10 Upgrade - Small Office Domain - Win 7 Proe OEM Licenses (~100 Machines):

    @Dashrender

    Have you tried your method without upgrading first?

    I have done them all thus far using install media, and it used to require that, but now no longer does. It just activates.

    Tried my method without upgrading? That was option two - no upgrade.

    I haven't tried installing my image, then placing the GenuineTicket.XML on the machine and seeing if it would activate, because I have a KMS server, and as soon as the VL media sees a KMS server, it self activates against that and Microsoft is completely unaware of the upgrade, so legally, I haven't upgraded my license from Windows 7 to Windows 10. - Will it still work? sure, is it legal - I'd say no.

    Now let's assume I had a none production network I could attach this compute to and put the GenuineTicket.XML file on my VL based image - I would still not expect that to work, MS changes the VL media, I would expect that to fail activate as it's a corporate version, just like Enterprise Edition is.

    Just like you couldn't put OEM codes in to VL media based installs. I just don't think it will work, so you're stuck doing either a full upgrade, or fresh install type upgrade with GenuineTicket.XML.



  • @Dashrender

    I just meant that at one point they were not accepting Win7 licenses to activate. You had to upgrade, register the Win10 machine. Then do a clean install.

    Then Microsoft changed that. Or at least it seems like they have to me.



  • @BRRABill said in Windows 10 Upgrade - Small Office Domain - Win 7 Proe OEM Licenses (~100 Machines):

    @Dashrender

    I just meant that at one point they were not accepting Win7 licenses to activate. You had to upgrade, register the Win10 machine. Then do a clean install.

    Then Microsoft changed that. Or at least it seems like they have to me.

    That is correct, when Windows 10 was released in July 2015, you HAD to upgrade (really you didn't, if you knew about the GatherOSState.exe trick you could have used that), but yes you HAD to upgrade.

    But enough people complained and said it's BS that they had to upgrade and instead they wanted to clean install, so MS changed the servers to allow you to upgrade by typing in the Win7 license key from the sticker.



  • @Dashrender said

    That is correct, when Windows 10 was released in July 2015, you HAD to upgrade (really you didn't, if you knew about the GatherOSState.exe trick you could have used that), but yes you HAD to upgrade.

    But enough people complained and said it's BS that they had to upgrade and instead they wanted to clean install, so MS changed the servers to allow you to upgrade by typing in the Win7 license key from the sticker.

    Perhaps I am doing this incorrectly?

    I have a Win7 Pro OEM license.

    I downloaded the Windows 10 ISO from Microsoft. (Not the OEM, per se, just the generic one which is all I have even seen offered.)

    I wipe the hard drive. I install Windows 10 from scratch. It activates.



  • @BRRABill said in Windows 10 Upgrade - Small Office Domain - Win 7 Proe OEM Licenses (~100 Machines):

    @Dashrender said

    That is correct, when Windows 10 was released in July 2015, you HAD to upgrade (really you didn't, if you knew about the GatherOSState.exe trick you could have used that), but yes you HAD to upgrade.

    But enough people complained and said it's BS that they had to upgrade and instead they wanted to clean install, so MS changed the servers to allow you to upgrade by typing in the Win7 license key from the sticker.

    Perhaps I am doing this incorrectly?

    I have a Win7 Pro OEM license.

    I downloaded the Windows 10 ISO from Microsoft. (Not the OEM, per se, just the generic one which is all I have even seen offered.)

    I wipe the hard drive. I install Windows 10 from scratch. It activates.

    that is the OEM installer.

    It just activates without the need for you to put the Win 7 key in from the sticker?



  • @Dashrender said in

    It just activates without the need for you to put the Win 7 key in from the sticker?

    So that takes the place of this step you posted from above? That is what has me confused.

    extract gatherOSState.exe from the install media, copy it to the desktop, run it, and save the GenuineTicket.XML file that it generates. Now format the machine and install Windows 10 from scratch, while completely disconnected from the internet. Before putting the computer on the internet, put the GenuieTicket.XML file in C:\ProgramData\Microsoft\Windows\ClipSVC\ directory, and reboot, while rebooting, put the computer on the internet.



  • @Dashrender said

    It just activates without the need for you to put the Win 7 key in from the sticker?

    Oh, was that a question? Yes. It just activates.



  • @BRRABill said in Windows 10 Upgrade - Small Office Domain - Win 7 Proe OEM Licenses (~100 Machines):

    @Dashrender said in

    It just activates without the need for you to put the Win 7 key in from the sticker?

    So that takes the place of this step you posted from above? That is what has me confused.

    extract gatherOSState.exe from the install media, copy it to the desktop, run it, and save the GenuineTicket.XML file that it generates. Now format the machine and install Windows 10 from scratch, while completely disconnected from the internet. Before putting the computer on the internet, put the GenuieTicket.XML file in C:\ProgramData\Microsoft\Windows\ClipSVC\ directory, and reboot, while rebooting, put the computer on the internet.

    yes



  • @BRRABill said in Windows 10 Upgrade - Small Office Domain - Win 7 Proe OEM Licenses (~100 Machines):

    @Dashrender said

    It just activates without the need for you to put the Win 7 key in from the sticker?

    Oh, was that a question? Yes. It just activates.

    So you never enter the key? and Windows 10 wasn't previously upgraded on this machine and then rolled back? i.e. Windows 10 has NEVER been installed on this machine before?

    There was a short period of time where OEMs were installing the Windows 7 Keys into the BIOS just like they do with Windows 8.x If that's the case, that would explain why you don't have to do anything - because as I mentioned earlier for Win 8.x, if it's in the BIOS, Windows 10 auto detects it and activates.



  • @Dashrender said

    So you never enter the key? and Windows 10 wasn't previously upgraded on this machine and then rolled back? i.e. Windows 10 has NEVER been installed on this machine before?

    Hmmm, now that you mention it, maybe I did install Win10 on it before.

    But I think I have done it before. On my own machine in fact.

    I will retract until I am 100% sure. 🙂


  • Banned

    You don't have to upgrade the windows 7 to 10 in place, Just image with a VL after you document and be done.

    Also depending on your level of volume licensing you don't need a seat for imaging either. Imaging rights comes with your agreement not the seat. The seat is just if you are at a lower level and don't get access to everything thin VLSC. (I'm guessing Open License & Open Value are the only two that need to buy this, not sure as we don't have too)

    Same with the documenting and going straight to windows 10, as along as you have an agreement higher than Open and Value you should be good. http://www.microsoftvolumelicensing.com/Downloader.aspx?DocumentId=9294



  • I have done a win7>win10 upgrades on about ten machines here at work. No major issues except when for people try to use Edge to do actual work. With 100 or so machines you could just login to each one and goto msn.com, hit the Upgrade button. Or unleash the update on your wsus, as youve suggested.



  • @Jason said in Windows 10 Upgrade - Small Office Domain - Win 7 Proe OEM Licenses (~100 Machines):

    You don't have to upgrade the windows 7 to 10 in place, Just image with a VL after you document and be done.

    Also depending on your level of volume licensing you don't need a seat for imaging either. Imaging rights comes with your agreement not the seat. The seat is just if you are at a lower level and don't get access to everything thin VLSC. (I'm guessing Open License & Open Value are the only two that need to buy this, not sure as we don't have too)

    Same with the documenting and going straight to windows 10, as along as you have an agreement higher than Open and Value you should be good. http://www.microsoftvolumelicensing.com/Downloader.aspx?DocumentId=9294

    SMB's rarely have an agreement higher than Open or Value, so that doesn't really play here.

    You only get imaging rights to the same version that you have OEM rights to on the machine, so for the SMBs here, they need to actually go through the License upgrade process, using any of the above mentioned ways, otherwise you're application of a VL image would be outside of your license agreement, even though with KMS or MAK it would work.


  • Service Provider

    I have done many remote upgrades via ScreenConnect. It has worked perfectly every time.

    I do grab the GenuineTicket.xml just in case though.

    My process.

    1. Download the current Windows 10 install using the Media Creation Tool.
    2. Extract GatherOSState.exe and save to some useful network place.
    3. Move the ISO to some useful network place.
    4. Go to or remote into user computer.
    5. Verify user data is backed up someplace.
    6. Run any pending windows updates.
    7. Reboot.
    8. Copy GatherOSState.exe to desktop and run as administrator.
    9. Move the GenunineTicket.xml to some useful network place.
    10. Delete GatherOSState.exe from desktop.
    11. Mount the ISO.
      a. If Windows 7, I will use VirtualCloneDrive to mount.
      b. Windows 8 mounts natively.
    12. Run setup.exe and follow the prompts.


  • @JaredBusch said in Windows 10 Upgrade - Small Office Domain - Win 7 Proe OEM Licenses (~100 Machines):

    I have done many remote upgrades via ScreenConnect. It has worked perfectly every time.

    I do grab the GenuineTicket.xml just in case though.

    My process.

    1. Download the current Windows 10 install using the Media Creation Tool.
    2. Extract GatherOSState.exe and save to some useful network place.
    3. Move the ISO to some useful network place.
    4. Go to or remote into user computer.
    5. Verify user data is backed up someplace.
    6. Run any pending windows updates.
    7. Reboot.
    8. Copy GatherOSState.exe to desktop and run as administrator.
    9. Move the GenunineTicket.xml to some useful network place.
    10. Delete GatherOSState.exe from desktop.
    11. Mount the ISO.
      a. If Windows 7, I will use VirtualCloneDrive to mount.
      b. Windows 8 mounts natively.
    12. Run setup.exe and follow the prompts.

    Since you're running setup from inside Windows 7, running the gatherOSState.exe shouldn't be needed, you're doing a traditional normal upgrade.


  • Service Provider

    @Dashrender said in Windows 10 Upgrade - Small Office Domain - Win 7 Proe OEM Licenses (~100 Machines):

    @JaredBusch said in Windows 10 Upgrade - Small Office Domain - Win 7 Proe OEM Licenses (~100 Machines):

    I have done many remote upgrades via ScreenConnect. It has worked perfectly every time.

    I do grab the GenuineTicket.xml just in case though.

    My process.

    1. Download the current Windows 10 install using the Media Creation Tool.
    2. Extract GatherOSState.exe and save to some useful network place.
    3. Move the ISO to some useful network place.
    4. Go to or remote into user computer.
    5. Verify user data is backed up someplace.
    6. Run any pending windows updates.
    7. Reboot.
    8. Copy GatherOSState.exe to desktop and run as administrator.
    9. Move the GenunineTicket.xml to some useful network place.
    10. Delete GatherOSState.exe from desktop.
    11. Mount the ISO.
      a. If Windows 7, I will use VirtualCloneDrive to mount.
      b. Windows 8 mounts natively.
    12. Run setup.exe and follow the prompts.

    Since you're running setup from inside Windows 7, running the gatherOSState.exe shouldn't be needed, you're doing a traditional normal upgrade.

    I believe i specified that I run in just in case.

    To clarify, I know 100% that it is not needed. But if any of the upgrades fail, have zero plan to start over, and the file may be needed.

    Never has yet though.



  • @JaredBusch said in Windows 10 Upgrade - Small Office Domain - Win 7 Proe OEM Licenses (~100 Machines):

    @Dashrender said in Windows 10 Upgrade - Small Office Domain - Win 7 Proe OEM Licenses (~100 Machines):

    @JaredBusch said in Windows 10 Upgrade - Small Office Domain - Win 7 Proe OEM Licenses (~100 Machines):

    I have done many remote upgrades via ScreenConnect. It has worked perfectly every time.

    I do grab the GenuineTicket.xml just in case though.

    My process.

    1. Download the current Windows 10 install using the Media Creation Tool.
    2. Extract GatherOSState.exe and save to some useful network place.
    3. Move the ISO to some useful network place.
    4. Go to or remote into user computer.
    5. Verify user data is backed up someplace.
    6. Run any pending windows updates.
    7. Reboot.
    8. Copy GatherOSState.exe to desktop and run as administrator.
    9. Move the GenunineTicket.xml to some useful network place.
    10. Delete GatherOSState.exe from desktop.
    11. Mount the ISO.
      a. If Windows 7, I will use VirtualCloneDrive to mount.
      b. Windows 8 mounts natively.
    12. Run setup.exe and follow the prompts.

    Since you're running setup from inside Windows 7, running the gatherOSState.exe shouldn't be needed, you're doing a traditional normal upgrade.

    I believe i specified that I run in just in case.

    To clarify, I know 100% that it is not needed. But if any of the upgrades fail, have zero plan to start over, and the file may be needed.

    Never has yet though.

    I have had GenuineTicket.XML fail and fell back to the Win 7 sticker - and that always works.



  • @JaredBusch said

    I believe i specified that I run in just in case.

    Computers. Shit happens. Good plan! 🙂



  • @BRRABill said in Windows 10 Upgrade - Small Office Domain - Win 7 Proe OEM Licenses (~100 Machines):

    @JaredBusch said

    I believe i specified that I run in just in case.

    Computers. Shit happens. Good plan! 🙂

    I wasn't doing it this way, I was saving the XML, then rebuilding with a Win10 USB stick, but that starting being rather unreliable. Switching to standard upgrade mode, while a little longer (oh and I had to say keep my user data, but no programs, as save nothing wouldn't register for me either) did work more reliably.


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