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    • #1324418
      Paolo Maffezzoli
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      I have in my environment several Windows 2008 R2 servers and I am planning to migrate to Windows 2019. I have read some Microsoft documentation and I am evaluating the in-place migration, according to How to In-Place Upgrade Windows Server 2008 R2 to Windows Server 2019 article is required an upgrade in different steps:

      • First, you upgrade Windows Server 2008 R2 to Windows Server 2012
      • Secondly, you will upgrade Windows Server 2012 to Windows Server 2016
      • Finally step, you upgrade Windows Server 2016 to Windows Server 2019

      Anyone tried to perform this upgrade process ? Any pros and cons from your perspective?

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    • #1324695
      Leos Marek
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      I prefer always clean installation. Have bad experience with in-place upgrade and that was just one jump, not 3 as described here.

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      • #1325397
        Paolo Maffezzoli
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        ok, I totally agree about a clean installation, in this case for certain small server a in-place migration could be an opportunity.

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    • #1325108
      Swapnil Kambli
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      Had the worst experience performing 2008 to 2016 in-place migration. 2008 to 2019 2-step in-place migration would need all sort of consideration and management.

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      • #1325384
        Paolo Maffezzoli
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        A possible intermediate solution could be a in place migration 2008R2 to 2012. Then evaluate next steps.

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        • #1325422
          Paolo Maffezzoli
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          but I would consider in place migration only in case of the safest choice, not just to run the fastest

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    • #1325111
      Swapnil Kambli
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      As noted in the article ‘As an alternative, you can also redeploy the applications on a fresh installation of Windows Server 2019.’. Even we had opted for the same solution for infra refresh.

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