How to upgrade Windows 2008 VM to Windows 2016

W2008Server VM SettingsHi,
 
 I have Windows 2008 Server as a virtual machine in Hyper-V 2016 Server and like to upgrade W2008 Server to W2016 Server.
What are the steps to upgrade?

Thanks.
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sgleeAsked:
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Andrew Hancock (VMware vExpert / EE MVE^2)VMware and Virtualization ConsultantCommented:
Quite simple really, it's not supported as an upgrade path!

If you really want to upgrade to 2016, you will need to upgrade from

2008 R2 --> Windows Server 2012 Standard/Datacentre --> Windows Server 2016 Standard or Datacenter.

and to do it, just put the relevant iso, in the cdrom driver and run the setup....

(please not do make a full backup before you start!) and be warned it may fail, or not be the same as you had with 2008!

Better off with a new 2012 server.
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sgleeAuthor Commented:
@Andrew,
 
This is Windows 2008 (not R2) Version 6.0.6002.
Can I upgrade this to Windows 2012R2?
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David Johnson, CD, MVPOwnerCommented:
Same process, don't suggest upgrade if this is a DC, remove the DC role first. if need be, stand up a temporary domain controller and migrate the roles over and ensure that replication works

Which version of S2K8 ? Standard, Enterprise, Datacenter? Must be the x64 version
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Andrew Hancock (VMware vExpert / EE MVE^2)VMware and Virtualization ConsultantCommented:
Even worse!
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arnoldCommented:
echo prior on how the upgrade path is just asking for trouble perhaps not right away but eventually.

Why carry baggage from prior os/setup potential mishaps.misconfigurations forward without a way back if  something goes terribly wrong.

Add a new VM, install the new OS on it. configure what you need on it. Setup what you need to setup, test to make sure it works as expected. Make DNS changes to now point to the new system. let the new VM take over the functions. Depending on what your application is, if the new only hosts the front end web portal, the data should still be accessible from the old/new.....

This way you have a fall back. if your upgrade path from 2008 to 2012 R2 succeeds, but your upgrade path to 2016 fails. you have to roll the whole thing back.

Do you have good backups? I.e. that you tried restoring in a test environment and they came up fine?
If you've not attempted the restores from all your backups, or do not have backups at all..........
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sgleeAuthor Commented:
Thanks for the comments.
The only reason I like to upgrade instead of setting up a new VM is because it is a terminal server. Setting up a new VM will be done in minutes, but it is going to take days to install & configure application software settings for every single user that connects to this machine.
I don't have to upgrade to Windows 2016. I will be happy with Windows 2012R2 because I think they are the same from performance standpoint.
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Andrew Hancock (VMware vExpert / EE MVE^2)VMware and Virtualization ConsultantCommented:
Thanks for the comments.
The only reason I like to upgrade instead of setting up a new VM is because it is a terminal server. Setting up a new VM will be done in minutes, but it is going to take days to install & configure application software settings for every single user that connects to this machine.
I don't have to upgrade to Windows 2016. I will be happy with Windows 2012R2 because I think they are the same from performance standpoint.

Correct, Terminal Servers need correct configuration, not just bodge it and run....

DON'T DO IT! and be a COWBOY!

Especially because it's a terminal server!

Good Luck, just stick in the CDROM, and click SETUP..... next next next.....finish and restart!

Wait for the users to call you.... it's not working....

Sometimes in IT, there are no quick shortcuts..... things need planning, design, test, rollout, more tests, feedback, fixes etc
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sgleeAuthor Commented:
@Andrew,
 "Correct, Terminal Servers need correct configuration, not just bodge it and run....
DON'T DO IT! and be a COWBOY!
Especially because it's a terminal server!
Good Luck, just stick in the CDROM, and click SETUP..... next next next.....finish and restart!
Wait or the users to call you.... it's not working...."

I am confused about the message ...  Are you saying I shouldn't upgrade?
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Andrew Hancock (VMware vExpert / EE MVE^2)VMware and Virtualization ConsultantCommented:
I would not recommend an upgrade.......but if you feel so inclined, those are the instructions, which you asked for.
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sgleeAuthor Commented:
Overwhelming opinion seems to be against the upgrade path.
I will keep existing W2008 terminal server as it is and take my time to install a new VM with W2016 and install/configure software for all the users.
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Andrew Hancock (VMware vExpert / EE MVE^2)VMware and Virtualization ConsultantCommented:
Best Decision
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