Upgrade MS 2008r Server to 2019 on a VMWare Server

[Ullskog]

Hi Im new on this, never worked with VMWare so bare with me.

Since the guy that can do this is to occupied with other things (they where 4 now hes alone) and I'm more Onsite-Technician I want to do my best to help him with things.

Today we have 3 VMWare Servers and on them we have a lot of virtual servers (MS 2008 mostly).

What I want to do is is copy one of the 2008r servers and then upgrade that one and see what will go wrong so we don't do it on a "live" server.

I now that we first need to upgrade from 2008r to 2012 and then to 2019.

Or is it easiest to install a fresh MS 2019 server and then migrate, for example I talking about a domain server?

Best Regards

Richard Ullskog
Sweden

[Alex_Romeo]

Hi,

I recently did the same activity.

Yes, the procedure to upgrade a Server 2008 r2 to 2019 is to perform the upgrade to 2012 R2 first.

If the Server does not have too many configurations, but simple services, you should make the update. If, on the other hand, Server 2008R2 has numerous applications with installed services, you should create a new one and then manage the migration.

If you proceed with the 2008-> 2012-> 2019 update, check first to verify that your installed programs and services are compatible with Windows Server 2019.

• Overview about Windows Server upgrades | Microsoft Docs
• Upgrade and Conversion Options for Windows Server 2016 | Microsoft Docs
• Aggiornare Windows Server 2012 R2 a Windows Server 2019 | Microsoft Docs (in Italian but the figures help).

At the end update , remember to change the version of the operating system from "edit settings" of vm.

ARomeo

[Ullskog]

Hi Alessandro

Thank you for your reply. I do think the best option after searching around a bit is to make e fresh install of a 2019r server and then migrate.

Now I only have to figure it out how to do it. :smileyconfused:

[Alex_Romeo]

Hi,

I turn you around these links that can be useful for the migration:

·        Migrating Roles and Features | Microsoft Docs

·        Download Microsoft File Server Migration Toolkit 1.2 from Official Microsoft Download Center

ARomeo