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The summary of the issue: Windows 10 Enterprise 2021 LTSC doesn't recognize a valid Windows 10 Enterprise 2016 LTSB license key and shows error code 0x80041014.

The long story:

I have bought a used Intel Compute Stick stk2m364cc that doesn't come with Windows from the factory (no OEM), but the previous owner has installed Windows 10 Enterprise 2016 LTSB on it.

Its activation status says it's a "digital license" (not linked to a Microsoft account). Also, I was able to extract the product key.

I would like to upgrade to the latest LTSC, so I have obtained en-us_windows_10_enterprise_ltsc_2021_x64_dvd_d289cf96.iso

According to some articles, I should be able to install the update for free because: "During the life of a LTSC release, you can upgrade your devices to the next or latest LTSC release free of charge using an in-place upgrade."

And LTSC is just renamed LTSB and essentially the same thing.

Here's what I did.

At first, I did a clean install of Windows 10 Enterprise 2021 LTSC, and it did not accept the key. This was my mistake, I should perform an in-place upgrade, as suggested.

So, I decided to step back and do an in-place upgrade. I obtained en_windows_10_enterprise_2016_ltsb_x64_dvd_9059483.iso and reinstalled it clean. It accepted the license key and activated it without any problems, so we can assume the key itself is good.

Then I launched the en-us_windows_10_enterprise_ltsc_2021_x64_dvd_d289cf96.iso installer from within Windows. I opted for a clean install removing personal data and applications. Was it wrong? Should I keep them to ensure the activation upgrade? Anyway, the install process worked almost till 70%, and then it suddenly popped up a small message box with the text: "Windows 10 installation has failed". No error code, nothing.

Looking for a fix, I found some articles explaining there's a Windows Setup problem with integrating updates during installation, and I should install with Internet disconnected. So I disabled my network connection and launched setup again. This time it was completed without any problems. It rebooted, I completed the setup, connected to Wifi, and went to activation. Initially, the status showed it couldn't connect to organization's activation servers. I ignored the error because 2016 LTSB also showed me the same error and it went away after I entered the key. However, 2021 LTSC tries to use the key and fails with a message that the key did not work, error code 0x80041014.

So, how do I update from Windows 10 Enterprise 2016 LTSB to Windows 10 Enterprise 2021 LTSC with the same license key? It should be possible without any local KMS, if 2016 was able to be activated without it, right?

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    "So, how do I update from Windows 10 Enterprise 2016 LTSB to Windows 10 Enterprise 2021 LTSC with the same license key?" - You don't. Those two versions are licensed independently. " It should be possible without any local KMS" - Windows editions that required VLK require a KMS.
    – Ramhound
    Commented Dec 19, 2021 at 19:27
  • How about you just buy a regular Windows license? Because it sounds to me like you’re not really authorized to use the license you’re currently using.
    – Daniel B
    Commented Dec 19, 2021 at 19:33
  • @DanielB That's a tricky question I guess. If an end-user buys a device with LTSB preinstalled, who owns the license and who has the rights to use the device. Commented Dec 19, 2021 at 20:18

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LTSB was renamed LTSC a few years ago, so we can essentially reference them successfully as the same product.

However, moving from LTSB 1607 to LTSC 1809 will require a different license, as the licensing isn't like Windows 10, more like Windows Server. LTSB is more closely related to Windows Server 2016, where LTSC is more like Windows Server 2019.

What is important here is how you purchased LTSB. If you purchased with Software Assurance, chances are you have access to LTSC products in the VLSC. If not, you likely need to purchase LTSC.

You need to contact Microsoft Support to find out if your LTSB license was bought with Software Assurance. If it was not, you cannot upgrade for free.

However, Windows 10 Enterprise 2016 LTSB can still be upgraded to Windows 10 Enterprise version 1607 or later, so this path is still open and free.

References:

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  • So, this article techcommunity.microsoft.com/t5/windows-it-pro-blog/… is wrong saying that "you can upgrade your devices to the next or latest LTSC release free of charge"? Or do they mean it like "you can upgrade for free, but only if you are authorized to get a new license key from Microsoft"? Commented Dec 19, 2021 at 20:21
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    They are right in the sense that you may install all LTSB updates freely on LTSB, as well as all LTSC updates on LTSC, just not upgrade one into the other.
    – harrymc
    Commented Dec 19, 2021 at 20:54
  • Thanks, that makes sense. Kinda. Microsoft has made it so confusing. They even have renamed 2016 to LTSC in some of their own articles, thus causing even more confusion and assumptions that there's no licensing difference between both: docs.microsoft.com/en-us/windows/whats-new/ltsc Commented Dec 19, 2021 at 21:10

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