Upgrading WinServer 2008

Question

Hello Guys

I have a WinServer 2008 and WinServer 2008 R2 version, I want to upgrade it to WinServer 2016.

Is it possible that I can directly upgrade WinServer 2008 to WinServer 2016 or I first have to upgrade WinServer 2008 to WinServer 2012 and then I have to upgrade WinServer 2012 to WinServer 2016?

Thanks

Answer 1

Not directly.
https://learn.microsoft.com/en-us/windows-server/get-started/supported-upgrade-paths#upgrading-previous-retail-versions-of-windows-server-to-windows-server-2016

An in-place upgrade is never recommended. Better option is to clean install, patch fully, migrate roles over to new instance of windows. You can also verify here and with manufacturer about operating systems support for the hardware.
https://www.windowsservercatalog.com/

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Answer 2

WINDOWS SERVER installation:
If you want to switch to a newer version of Windows Server on the same hardware, one way it always works is a clean installation, where you simply install the latest operating system directly on the old one on the same hardware, thus excluding the previous operating system. This is the simplest way, but first you need to back up your data and prepare to reinstall your applications. There are a few things you should know, such as system requirements, so check the details of Windows Server 2016, Windows Server 2012 R2, and Windows Server 2012.
Switching from any pre-release version (such as Windows Server 2016 Technical Preview) to released version (Windows Server 2016) always requires a clean installation.

Ideal would be to back up the files and after formatting for removals of vices and excess remaining files. Install all software again.

Link: https://learn.microsoft.com/pt-br/windows-server/get-started/installation-and-upgrade

Hugs
Mr. Iraè César Brandão

Answer 3

Is it possible that I can directly upgrade WinServer 2008 to WinServer 2016
No, you need to upgrade Windows Server 2008 R2 to Windows Server 2012 R2 firstly, then upgrade Windows Server 2012 R2 to Windows Server 2016/2019
However, if you have the option to do a clean install and migrate, I suggest to choose this route. Upgrades should be a last resort where possible.
If you still insist on in-place upgrade, this Microsoft article can help you.
https://techcommunity.microsoft.com/t5/itops-talk-blog/how-to-in-place-upgrade-windows-server-2008-r2-to-windows-server/ba-p/752330

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