Upgrading from Windows Server 2008 to Windows Server 2016

Kasey Hart
Kasey Hart used Ask the Experts™
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Do you have to take intermediate steps in upgrading to Windows server 2016, or can you upgrade directly?
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Adam BrownSenior Systems Admin
Top Expert 2010

Commented:
By upgrading, what do you mean? Upgrading the OS on the server or replacing the server with a new one?
Kasey HartBusiness Development

Author

Commented:
Adam, We want to upgrade from Windows server 2008 to Windows server 2016 by upgrading the OS on the server.
Senior Systems Admin
Top Expert 2010
Commented:
Okay. In that case you do need to upgrade to 2012R2 first.
Scott FellDeveloper & EE Moderator
Fellow 2018
Most Valuable Expert 2013
Commented:
I am looking to do the same thing but going from 2008 to 2019.  MS is saying you can go directly from 2008 and the upgrade is taken care during the installation process.  However, I am only using this as a file server and nothing else. Essentials version is $500 and I am considering just switching out the server for a Synology NAS server as that would be about the same price and easier to manage.
kevinhsiehNetwork Engineer

Commented:
Is the OS 2008 and 32 bit? If it is, the process is simple, because you can't. If your starting point is actually 2008 R2, then it is 64 bit and upgrade is possible. If the OS is 2008 but 64 bit, then upgrade is possible.

That said, any machine running 2008 is likely physical and running on old hardware. I would highly recommend a fresh install as a VM on more modern hardware. What is the reasoning for wanting to do an in-place upgrade?

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