You need to upgrade to 2012 R2 or 2016 first. Then you can upgrade to 2019. 
Everything can happen “in-place”. Do a Windows System Backup beforehand (e.g. 
to a USB drive) if you’re worried about it all dying in the middle.
Make sure that your hardware is supported under 2019 – 99% is.

Regards
Ken

From: [email protected] <[email protected]> On Behalf 
Of Greg Keogh
Sent: Thursday, 27 December 2018 6:08 PM
To: ozDotNet <[email protected]>
Subject: [OT] Server 2008 R2 to 2019

Hi folks (quiet in here lately... where is all the .NET chatter these days?)

My home office LAN has a Windows 2008 R2 server running on a real box. It only 
does two things:

1. It's the domain controller.
2. It runs my 2008 R2 web server inside Hyper-V.

I'd like to update the 2008 R2 DC to 2019, just so I have the latest for 
testing and learning. However I have never before upgraded or replaced a DC and 
I'm not sure what the easiest path is. I could just wipe and install 2019 and 
set the DC feature, but all the AD tree of computers and users would be gone 
and all the authentication and ACLs all over the LAN would be cactus (I think).

Is there some ay of upgrading my DC with the least suffering? Any general 
advice would be most welcome.

Cheers,
Greg

P.S. I must be marginal, as Santa just gave me socks, undies and Bunnings 
vouchers … nothing IT related. Anyone get any good tech?

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