Migration of Windows 2012 Essentials (non r2) to Essentials 2016 or 2019 (futureproof)

Question

Hi,

I've looked through the forums/QA regarding my topic and since i couldn't find any i'm hoping someone can help me here.

A client of mine currently has a Windows 2012 Essentials server running 10 users and 15 devices connected to it. Next to it is a very old Windows 2008 server running as an application server for the financial system. To keep everything secure and healthy they should upgrade. First goal is to decommission the old win2008 box and plan to do something with the 2012 Essentials machine. We have already ordered a new Dell server with 64Gb of memory, 8 Tb disk and a Windows 2019 standard (16 core) license on it

My plan is to install it as a HyperV host and to install a Windows 2019 standard guest on it to host a new application server. I guess quite simple. My first question is whether I should join the HyperV host to the Windows 2012 Essentials domain of to just keep it as a workgroup machine. I think i've read that it's better to join it because of integration with RDP etc. Does anyone have any thoughts on this? Also maybe depending on my second question on whether to keep the 2012 Essentials domain in place

Now maybe for my bigger second question; how to migrate the Windows 2012(non R2) Essentials machine to a more future proof situation. I know that Essentials 2019 does not have the experience role anymore. So no RDP/Remote access, Client backup or centralized dashboard. However it is still an interesting license model for my client ( < 25 users and <50 devices) so in guess still a viable option. Another option would be to go to Windows 2016 Essentials and keep all the essentials stuff and postpone the decision on what to do with the Essentials functionality. Or is this my only option as I read here: https://learn.microsoft.com/en-us/windows-server/upgrade/upgrade-overview

Let's say I go with the migration to the 2016 Essentials; could this be possible to do in a virtualized way? Could I just install a new virtual machine with Windows 2016 Essentials and do a migration from the 2012 (nonr2) Essentials machine? (basically still this guide https://learn.microsoft.com/en-us/windows-server-essentials/migrate/run-the-windows-server-essentials-best-practices-analyzer) Is this guide still ok for this and is it possible to go from 2012 Essentials (non r2) to 2016 Essentials? I would need a 2019 Essentials license for that i guess (with downgrade rights) and then be permitted to run it on the hyperv host with it's own std 2019 license?

Or is a better option to just create an entire new domain within either 2016 essentials or 2019 essentials and manual migrate everything over. Basically what is said here : https://social.msdn.microsoft.com/Forums/en-US/8ded44d3-7da4-456d-b1c8-796a6d6afd8a/upgrade-windows-server-2012-essentials-to-2019-essentials?forum=winserveressentials . In this case I am wondering if it's wise to join the new HyperV host server to the existing 2012Essentials domain as it will be replaced lateron. Does anyone here have a similar experience? So basically a 2012Essentials domain wanting to virtualize and keep within the Essentials licensing model?

So basically to summarize
current:
Box1: Win2012Essentials
Box2: Win2008

future:
Box3: Win2019std With HyperVRole
Box3.1: Win2019std Guest
Box3.2 Win2016Essentials

Question1: Should a hyperv host in a essentials domain be domain joined?
Question2: Can a Hyperv std licensed host run a guest Essentials 2016/2019 (with 2019 essentials license)
Question3: Is a migration possible from 2012(non-r2) to Essentials 2016 or am i forced to recreate the domain. And the impact on the hyperv host

I guess it's a quite common scenario for a business to have and plan to go with virtualization in the future so I hope someone can help me with some advice/experience. Sorry for the large amount of text :)

Thanks for any input. Regards, Martin

Answer 1

Question1:

Should be fine either way. Joining domain may make administration simpler.

Question2:

Should not be a problem but you'll need a valid product key for activation.

Question3:

you can follow along here.
https://learn.microsoft.com/en-us/windows-server-essentials/migrate/migrate-server-data-to-windows-server-essentials

--please don't forget to Accept as answer if the reply is helpful--

Answer 2

Hi @Anonymous , thank you for your quick response.

Regarding Question1: I think i will go ahead and do this. There seems to be a lot of discussion about it but it seems that consensus is going towards your answer. The issue people bring up is the risk of the guest domainserver not being 'up' while the host boots eg. But I think I read this should not be an issue really. Do you concur?

Regarding Question3 : During my search I also found this section of documentation. The confusing part is however that there is no real guide of 2012 Essentials to 2016 Essentials. It's always about R2. I guess there is no difference? Do you know from experience that it will work and that the guide is basically this: https://learn.microsoft.com/en-us/windows-server-essentials/migrate/migrate-from-previous-versions-to-windows-server-essentials-or-windows-server-essentials-experience

This looks like the same procedure as i've done before migrating to this current 2012 Essentials from their previous SBS2003 server. Is that correct?

Thanks again for your time. Really appreciated.

Martin

Answer 3

risk of the guest domainserver not being 'up'

That's really a non-issue since cached credentials should work or worst case use a local account to logon.

there is no real guide of 2012 Essentials to 2016 Essentials

Yes, the steps are still the same.

--please don't forget to Accept as answer if the reply is helpful--