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Deploying image results in Windows 10 NOT activated

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I have a number of Windows 7 Pro machines.  They are HP desktops and laptops.  About a half of them are older than 2014, and therefore have the Microsoft Genuine Label sticker with the product key.  I am in the process of upgrading these machines to Windows 10.  The process I have been trying to follow is as follows:

1.  Create an install DVD using the media creation tool
2.  Install vanilla Windows 10 using the DVD and putting in the Windows 7 product key from the sticker
3.  Ensure that Windows 10 activates (with digital rights) after installation

Now, these machines have a bunch of software and configuration on them, and I want them all to be the same.  So I take one as a "master" and do all the setup and configuration on that one.  Then I use Snap Deploy 5 to take an image of the master, which I then deploy to the other machines.  All the desktops are the same hardware, and all the laptops are the same hardware, so I actually create two "master" images.

The image is deployed without any issue at all.  However, when I take a look at the newly-imaged machine, the Windows is not activated.  And if I try to activate it with the Windows 7 key, it says that key can't work for this product.

I have opened tickets with Microsoft and they have helped me to activate two of the imaged machines.  However, they are only able to do this one-by-one (since the machines have retail licenses), and it takes forever.  

My question is:  is there a way to image the machines WITHOUT losing the activation?  I understood that activation should be automatic for a machine that was already activated before and which didn't have any hardware changes.  However, it doesn't seem to work when the reinstallation is an image.

Any pointers would be much appreciated.

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Joseph.

The Windows 10 upgrade licensing is a limitation of Microsoft/Windows.  In order to activate Windows 10 licensing as an upgrade, you must actually upgrade each machine manually one time.  This is a pain, but no way around it.  Once upgraded, the hardware is then licensed with Windows 10 indefinitely and then you can push the same image to all of the machines and they will be licensed after image deployment or after a fresh install.  The key is, you must upgrade the old OS once first and must do this on every machine.  Upgrade ends on the 29th so not much time left...

https://support.microsoft.com/en-us/help/10751/windows-10-why-activate

You created media and performed a clean installation of Windows 10, instead of first upgrading from your previous version of Windows

In order to upgrade to Windows 10 using the ISO image or upgrade media you created using the media creation tool, you need to select theUpgrade this PC now option. 

If you performed a clean installation instead of an upgrade, you'll be asked to enter a Windows 10 product key or buy a new license in order to activate Windows 10. This is because we weren't able to register your free upgrade entitlement with the activation servers because you didn't upgrade to Windows 10. To fix this, you'll need to go back to your previous version of Windows, make sure the previous version is activated, and then upgrade to Windows 10.

I guess the machine from which the image is taken also has to follow the same process?  Meaning, it has to be upgraded from a Windows 7 Pro to a Windows 10 Pro, then the image taken, and then the image deployed to other machines which have already been through the same process?  I ask because my master image machine was upgraded using a fresh install using the media.  Windows is activated on that machine (because I never had to apply an image to it).  But when I tried to apply that image to another machine which had been upgraded to Windows 10, then it doesn't activate (same as my original situation).

Hi Joseph.

I have not had this experience - are you 100% sure this particular machine was upgraded to Windows 10 and showing it was licensed already?  I could see that it might not originally show as licensed when you redeploy an image, but should sort itself out after some time - perhaps reboot a few times and check again.  Also, go to Settings >>> update and security >>> activation and see what it says.  Then check in "computer" (right click) >>> properties and click on the license at the bottom and see if you can get it to check in again.  

Did you try generalzing the hardware and/or SID when you deployed the image?  if not, try one, then the other, then both and see if that helps at all.  

As long as the hardware you are deploying the image to has been previously licensed to Windows 10 via the upgrade method, any Windows 10 image you deploy to that previously licensed hardware should automatically license too (assuming you are deploying the same OS version like home to home or pro to pro - if trying to deploy a pro license on a sytem that was upgraded to Windows 10 Home, this won't license either).  

If all else fails, you can check with Micorosft to see if they can verify if the hardware you are deploying the image to already has a digital entitlement registered for the upgraded.  

For the master image machine, here is what I had done.

1.  I downloaded the media creator tool from the Windows 10 upgrade site for offline upgrade
2.  I used the media to do a clean install of Windows 10.  I was prompted for a Product Key, and I put in the Windows 7 key that I had for that machine
3.  I proceeded to complete the installation, and when it was done the Windows installation showed as Activated

So, no I didn't first upgrade the machine like you advised.  In the meantime I created a new master image based on a machine that was actually upgraded first as you advised.  When I drop that image on another machine which was properly upgraded, then it works.  So I will proceed to bring the machines back to activated Windows 7 (I have several old images which work for this purpose).  Then do the proper upgrade on all of them.  Then drop the new image.

Thanks for the guidance.  It has been extremely helpful.

Glad to be of help.  Good luck with the upgrades. 

Hi, I am trying to create a windows 10 master image but I am having some issue. I am trying to install the management agent on the client laptop but I get an error Failed to connect. All firewall settings has already been turned off. Please help.

Hi John, I'd suggest contacting Acronis technical support if it's not installing correctly.  In the past, I would have users uninstall from control panel, run the True Image cleanup tool, reboot and try to install again - making sure to right click and "run as administrator" when launching the installer (that's the only way to give full admin access for the install - even if logged in as admin and you get the UAC prompt to continue as admin).

Here's the link to the cleanup utility - even though it's not for Snap Deploy, it seems to cleanup pretty much all Acronis products.  https://kb.acronis.com/aticleanup#Windows0