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Error In-Place upgrade Hyper-V Core 2012 R2 to 2019 [SET_PRODUCT_KEY operation failed]

Szunomár Péter 46 Reputation points
2021-08-24T13:34:19.007+00:00

We have a Hyper-V cluster of 4 host running Hyper-V Core 2012 R2. I should upgrade them to 2019.
At the first host i stuck with a problem. All the VM-s are stopped and I'm trying to do an in place upgrade, but it only throws an error

0x80070490 - 0x2000E
The installation failed in the SAFE_OS phase with an error during SET_PRODUCT_KEY operation.

The 2012 R2 is domain joined and fully up to date, I'm connecting to it with a domain user. The iso of the 2019 is the fresh version newly downloaded from my.visualstudio.com

What is wrong and how next?

Hyper-V
Hyper-V
A Windows technology providing a hypervisor-based virtualization solution enabling customers to consolidate workloads onto a single server.
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  1. Dave Patrick 426.2K Reputation points MVP
    2021-08-24T13:58:29.56+00:00

    Most likely the underlying OS is corrupt / broken in some manner. The cleaner / much safer method is to stand up a new one, patch fully, migrate roles over to it.

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

  2. Limitless Technology 39,436 Reputation points
    2021-08-25T09:36:15.907+00:00

    Hello Szunomar P,

    Had exact same issue.

    Resolved it by using the KMS Client Setup Key during upgrade.

    KMS client setup keys

    Specifically this one:

    Windows Server 2019 Datacenter WMDGN-G9PQG-XVVXX-R3X43-63DFG

    On the other hand In-Place Upgrade is not a great idea. Microsoft does not support In-Place Upgrade and must be a good reason with that. The best practice, specially in the case of HyperV Hosts is to migrate the VMs from host to host:

    -Shut down VMs
    -Merge any checkpoints
    -Export VMs to shared drive on new hardware
    -Import into new host
    -Update Hyper-V services on VMs
    -Boot App server and test before booting AD
    -Decommission old hardware

    Hope it helps you!

    Do not forget to vote if helpful or mark as an answer if it resolved your query!

    Best regards!

    Luis P

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