Windows 10 Pro upgrade/activation process

I support 60 Windows 7 Pro laptops.  I want to upgrade them all to Win 10 Pro.  The problem is when a laptop comes in from the field and needs to be re-imaged.  So before we mass upgraded, I ran a few tests.

·        When an activated Windows 8.1 Pro or Windows 7 Pro laptop is upgraded to Windows 10 Pro, the upgraded copy of Windows 10 is activated and the motherboard is logged by MSFT;

·        Therefore whenever that computer breaks, we can re-image the hard drive with our Windows 10 configuration, and the MSFT database then activates that image based on the motherboard.  We do not have to keep or track license keys.

Actual experiment:
·        I upgraded a Windows 8.1 Pro to Windows 10 Pro;

·        I verified that the now upgraded copy of Windows 10 Pro was activated in System (therefore it should be in MSFT’s database and it doesn’t matter what happens to the hard drive.  Any copy of Windows 10 Pro applied to this laptop should auto-activate forever);

·        I then imaged this laptop with our Windows 10 Pro configuration to the laptop;

·        I verified internet connection and waited for auto-activate to occur;

·        It did not auto-activate;

·        I clicked on the Activate options and the only choices were to input a new license key;

·        I confirmed the laptop was connected to the internet, and left it on all night;

·        The imaged copy of Windows 10 Pro did not activate.

Based on this experiment, if we upgrade all of our laptops to Windows 10 Pro, and any of them has a failure and must be re-imaged, then none of them will auto-activate.  It appears we need Windows 10 Pro license keys to make this work.  Our understanding was that we didn’t need license keys anymore and that the upgraded Win 10 was linked to the motherboard.
Can you help me understand how MSFT licensing works so that we can upgrade these laptops, and then when failures occur, have activated copies of Windows 10 Pro using a stored image?

footnote:  we use Acronis to create a master image.  We have done this with Win XP, with Win 7, and with win 8.1.  whenever a failed laptop comes in, we just re-image it with Acronis, then put in the license key.  According to MSFT, this is no longer necessary, and MSFT keeps a record of activated Win10 copies by associating a token with the serial number of the mother board.
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Cliff GaliherCommented:
You'll have this issue if you are creating or using a custom image. Re-imaging rights has always been a VL benefit and continues to be. If you want to take advantage of the free upgrade offer, you'll need to stick to stock upgrade media. Note that windows 10 now has tools to apply "packages" after install to standardize corporate deployments, so customizing an image is usually not necessary.
LEECHIPTURNERAuthor Commented:
When you say stock upgrade, you mean just off the shelf Win10 media?  So, pretty much, our custom image is no longer usable?  What would be the process if a dead hard drive comes in?
Install hard-drive;
Use Win10 media to install Win10;
Would it auto-activate after install?

Sounds like what I have to do is this:
Upgrade each laptop individually;
Check to verify that it activated;
Create an image of that hard-drive;
Then if it ever comes back in for a failure, I install the hard drive, and put that specific laptop's image back in it.

Therefore, I will need to upgrade 60 laptops, then create 60 images.  Correct?
Cliff GaliherCommented:
When I say stock upgrade media, I mean the media you can create using the Microsoft media creation tool, which is available from the windows 10 download site.  Yes, your custom image is no longer usable unless you purchase windows 10 via volume license. That is both a technical and legal limitation. You don't have re-imaging rights, so even if you got a custom image to work, you'd be in an illegal state. And if you buy VL, you would get keys, so you wouldn't be relying on the automatic "free" upgrade path.

Yes, you do have to upgrade each laptop individually. That is nothing to do with the image, but everything to do with registering the hardware with Microsoft for the free upgrade.  Yes, you have to check that it is activated.  You do *not* need to create an image of the hard drive, nor do you have to eep 60 images. You'd simply install Windows from the clean upgrade media, and it'd properly auto-reactivate just like your initial assumption as written in the question.

The failure is coming because you didn't re-install with clean media. That's it. That's the entirety of the problem.
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LEECHIPTURNERAuthor Commented:
I will test that and see if it works.  Since I have upgraded one laptop, I should be able to format its hard disk, and then using stock media, re-install Win10, and it should activate.  Hope it works!
It should also be noted, that as of today, Win10 TH2 (Build 1511) is out and downloadable.
It is said to accept win7 and 8.1 keys right away, no need to upgrade install anymore.

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LEECHIPTURNERAuthor Commented:
McKnife, seriously?!  That would solve all my problems!  Do you know this for a fact (accepts 7 & 8.1 keys)?
I just installed one instance in a vm using my win7 key, works.
LEECHIPTURNERAuthor Commented:
Ahhh, McKnife, once again life is peaceful and serene!  I recant all the evil things I said about Microsoft.
Already closing?
Are you sure that you have won? Before, you could not use your standard image to resurrect an already activated, defective win10. Now?
LEECHIPTURNERAuthor Commented:
Downloading 1511 now.  I will create the image using 1511.  Then blast it onto a Win7 laptop and see if I can activate with the Win7 key.  If so, I'm back to my original process... one image to rule them all!  If not, then I am back to Cliff's solution, which will be workable but VERY time consuming.  So there are only two solutions... I Googled 1511 and you were right.  I'm keeping my fingers crossed.  Do you know if I create an iso using the media creator, if it will be 1511?  I'm assuming so.
Yes, will be, at least if you take the current media creator exe.
Cliff GaliherCommented:
There are two things to consider here:

1) Even if you can technically activate a custom image with a win7 key, you are not legally entitled to do so unless you have purchased win10 via volume licensing. So the root cause of your initial problem was the custom image, and it still is.

which plays into...

2) The free upgrade is *only* available for a year. If you install win10 "clean" on July 30th, 2016 and try to activate it with a win7 key, it will fail given the current policies for the free upgrade offer. And the re-activation after a legitimate upgrade still requires "clean" (not custom) media, which was the *entire* issue you had with your test.  Re-activation is based on the hardware registered with Microsoft, not with the key you enter during the initial install.

So this 1511 change eases the initial upgrade process, yes. But your question wasn't about upgrading 60 PCs. It was about how you'd handle re-activating a PC if you ever need to re-install. And from a DR standpoint, relying on win7 keys to re-activate is not a good plan, as the shelf-life for that is about 7 more months, max.
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