Upgrading Windows Server 2008 R2 to 2016

Overview

You cannot upgrade to Server 2016 from 2008 R2 without losing all the files and settings. You need to upgrade to 2012 R2 first. I have demonstrated a way that it can be done

Upgrading to 2012 R2 from 2008 R2

Upgrade to 2012 R2 first. 

If you are upgrading a DC, ensure to perform adprep.exe /forest prep followed by adprep.exe /domainprep. This is run from the D:\sources\support\adprep folder from the Windows 2012 R2 media.

Proceed to start the setup to keep files and settings.

You can keep it in trial mode and add the licence once upgraded to 2016.

Upgrading to 2016 from 2012 R2

If you are upgrading a DC, ensure to perform adprep.exe /forestprep followed by adprep.exe /domainprep. This is run from the D:\sources\support\adprep folder from the Windows 2016 media

Proceed to start the setup to keep files and settings.