Configuring WSEE on Windows Server 2019 Standard


I have a Windows 2012 R2 server installed with the Essential role.
I want to upgrade the network to Server 2019 and then decommission the 2012 server.

So I installed a clean Windows server 2019, joined it to the domain, installed DHCP, and imported the CA root from the 2012 R2 server. I then installed the AD role to the server. When I try to configure the WSEE role, the wizzard complains that the domain already exists.

Any idea why this occurs and how I can work around this issue?

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Good Answer

Alas, I’m afraid that I’ve never gone down that road before (seeing as I ALWAYS recommend that folks start off with a brand new/clean out-of-the-box installation of Windows Server 2019 Standard/Datacenter for the best results). From the sounds of it, you are going to need to do an in-place upgrade from Windows Server 2012 R2 to Windows Server 2016 first, and then another in-place upgrade from Windows Server 2016 to Windows Server 2019 after that. From there, you can then install WSEE on Windows Server 2019.

For more info on why you need to in-place upgrade from 2012 R2 to 2016 to 2019 see what I’ve said over here.

However, you might be better off doing a domain-migration instead. Microsoft has the steps that you will need to take in order to do that listed over here:

Step 2: Install Windows Server Essentials as a new replica domain controller

And, another user has very kindly posted the steps that he took for doing a successful domain migration here.

I hope that helps you out some.

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