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After doing a lot of research, I didn't find the exact answer to my question.

We are currently using Windows Server 2008 R2 and we intend to switch to Windows Server 2019. For obvious reasons of scalability, redundancy and performance, we want to use virtualization to virtualize our new Windows Server and we will be starting from scratch and not migrating anything from old install

Unfortunately, I don't know how to start. I have my Windows Server 2019 ISO with the server mounted. Should I install WS2019 with a Hyper V role that will virtualize a new WS2019, or, should I install a Hyper V server where I virtualize WS2019, or install a nano server with a Hyper V role in WS2019 virtualization.

While researching, I feel that the first solution seems to be the most considered, however, I am wondering about updating and maintenance. Indeed, in the first solution I will have a double OS layer to update whereas the other two solutions will be much simpler in maintenance.

What do you think about it? Is there something I haven't thought of? How do you do it? What are your arguments?

Dave M
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slieu
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As mentioned by Greg Askew in the comments, Windows Nano is only for Containers. in my organisation we don't use Hyper-V but your considerations are pretty much spot on except you will want to also consider management of the Hyper-V instance.

If you run Hyper-V server, its a cut down OS and the interface is quite minimal. Remote management is where its at for this kind of system and Windows Admin Centre is getting more and more features to make this more reasonable. https://docs.microsoft.com/en-us/windows-server/manage/windows-admin-center/use/manage-virtual-machines

The other consideration you have to take into account is licensing. Work out which one is better for your company in the long run for licensing. If you do WS + Hyper-V will this have more licensing implications vs running Hyper-V and then installing the VMs and licensing them?

Laywah
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