Upgrading Windows Server 2008 Standard (32-bit) to Windows Server 2016 Standard (64-bit)

I’m trying to upgrade my windows server 2008 standard 32-bit version to windows server 2016 standard 64-bit version. The server is currently running as a secondary domain controller as the primary has failed. I was hoping I could do an in place upgrade but I am now realizing that upgrading from the 32-bit to the 64-bit is not possible.

If I were to reformat and start fresh what would that mean for all my workstation computers? If I remove all of my machines from the domain, do the server upgrade, and then re-join all the machines to the new domain does that mean there’s going to be new profiles on every workstation computer and thus seem to the end-users as though they have brand new machines or after re-joining the new domain (with the same name) will their existing profiles continue to act as they did before?

Lastly, depending on the answer to the previous question should I be doing an upgrade from windows server 2008 to windows server 2012 R2 and then an update to Windows server 2016? Or upgrade to Windows server 2012 and then update to windows 2016? The question being that I don’t think I have windows server 2008 R2 so should I be going to windows server 2012 R2?

Solution 1:

You'll want to set up another domain controller and migrate the crucial AD roles to it. Then you can demote the old server, reinstall it and set it up as secondary DC. Don't forget to upgrade the AD version to something recent.

Of course, you can also install completely anew and start from scratch. That would also mean to set up new user accounts on all your workstations after rejoining them. Yes, that means all new user profiles as well.

Since you cannot upgrade from a 32-bit Windows server to a 64-bit edition, your stepped upgrading is moot (2012R2 onward is 64-bit only). Directly install the version you're planning to use.