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In our company we are planning to do Windows 2008 R2 migration due to End of Support it reached. We're not that fans of living on edge but this time it appear to be wiser target to Windows Server 2019, not 2016 (so we'll live with for years further).

While reading on this topic and looking for best practice approaches I can see many people recommend to do step-by-step migration (2008R2 -> 2012 -> 2016 -> 2019), but in our case it appears to be very lengthy and error-prone way, isn't it? At the same time, looks like we can do that in one giant step (2008R2 -> 2019) so I would like to ask your advice, is it true?

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  • I have tried to do 2008R2>2019 directly and it did not work. I had to step, though I did 2008R2 > 2012 > 2019. – Narzard May 6 at 13:42
  • Dear @Narzard thank you for you answer, did you tried AD scheme upgrade 2008R2>2019 or Windows Servers that were domain controllers in 2008R2 domain? I don't want to bother with upgrading servers, I just want to add new (2019) Servers into old domain, then move roles to it and then remove old (ex) DCs from domain and then upgrade the domain. THANK YOU! – Alexander May 6 at 14:26
  • no, they were not servers on a domain. – Narzard May 6 at 14:34
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According to Microsoft's Upgrade Scenario Planner, you must upgrade to Windows Server 2019 from Server 2008 R2 in three steps:

  1. Upgrade to Server 2012
  2. Upgrade to Server 2016
  3. Upgrade to Server 2019

There's no way around this. Attempting to skip one of these steps will not work because the installer for the new version of Windows Server will refuse to run if the prior version is not supported for upgrade.

  • The idea I mess with is this: I can upgrade Windows Server itself OR I can upgrade AD only by installing newer (or newest, 2019) version of Servers on separate VMs, add it to domain and move roles to it one by one, so I'll end up with duplicate VM for each of my old DCs with roles completely on it. Then, as all roles be moved to new Servers, I can do the scheme upgrade, isn't it? Thank you for your advice! – Alexander May 6 at 14:21
  • Yes you can install a 2019 server in your domain, promote it to a DC, transfer all of the AD roles to the new DC then un-promote your old server. That's obviously a simplified description of the process. – Twisty Impersonator May 6 at 15:01
  • Twisty Impersonator this way I can skip these steps, right? – Alexander May 6 at 15:03
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    Based on your comments I can see that your actual question is how to migrate your domain controller to server 2019 in the fewest steps possible. Your original post is not clear on this point. My answer above answers how to upgrade a 2008 r2 server to server 2019, which arguably is what your original post seems to ask. That said, yes, since you don't have to do an in place upgrade of your existing domain controller, you can skip the intermediate server upgrade steps. – Twisty Impersonator May 6 at 19:06

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