Following on from my video upgrading Windows NT 3.51 all the way up to Windows 10 I have a new video for you. In this video I start with a virtual machine running Windows Server NT 3.51 and upgrade it all the way up to Windows Server 2019. For servers the upgrade is as simple as clients, Windows NT 3.51 to Windows Server 2003 the OS was 32bit but from 2008 onwards Windows Server is 64bit so I had to do a dual boot at Windows Server 2003 to switch to the 64bit.
In the video I show the upgrade from Windows Server NT 3.51 to NT4, 2000, 2003 and then the switch to 64bit and continue on with 2008, 2008R2, 2012, 2016 and then ending up on Windows Server 2019 with files from the original install. I did have a BSOD at one point; I had to turn off Hyper-V backward compatibly for the VM to fix it.
Who knew you could have so much fun with Hyper-V and Windows Server!