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Migrating from Windows Server 2008 R2 to Windows Server 2019 Essentials

I'm seeking step-by-step advice on migrating an on-prem Windows Server 2008 R2 server to a new on-prem server running Windows Server 2019 Essentials.  The client has fewer than ten users, so Essentials seems the appropriate version for them.  Their 2008 server is a Domain Controller.  It's their only server.

I'm asking for the list of steps that move the old server files and configuration, including the Active Directory configuration, to the new serve.  Thanks, Experts!
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Distinguished Expert 2019

Commented:
The files could be copied using dfsr.
Look at dfsmig whether your sysvol uses FRS or dfsr.

You would need to use intermediate server 2012/2016 before you can get to server 2019.
John AtkinsonIT Consultant

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Commented:
arnold, do I need to worry about going through 2012 and 2016 if I’m moving to new hardware?  (I thought I only had to be concerned about the intermediate versions if I was planning to upgrade the OS in place on the old server.)
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Commented:
Going through intermediate steps deal with two separate tracks
1) server upgrade path which you analyzed correctly,
2) deals with maintaing and transferring existing AD versions. 2008/r2 to 2012/2016 no direct path to 2019, then the 2019 can be joined when the AD forest/domain level is at least 2012 and sysvol replication relies on dfsr.

The difficulty since you chose essentials, you can not setup a domain trust to start a new domain on the 2019 ....
John AtkinsonIT Consultant

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Commented:
arnold, can you elaborate on the steps comprising these two separate tracks?
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Commented:
You are not going in place upgrade because you are going to different version.




Make sure your current sysvol is setup for dfsr based.
Using the tools on the 2019 DVD, you need to run the adprep to update domain, schema, GPO


Look at the following, it seems it might be possible to add a Windows server 2019 as a DC .
https://serverfault.com/questions/955401/how-to-add-windows-2019-server-to-2008-r2-and-migrate-dc

Which current clients do you have?
John AtkinsonIT Consultant

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Commented:
arnold wrote: Which current clients do you have?

I'm sorry, but I don't understand your question.
John AtkinsonIT Consultant

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Commented:
arnold, in case you were referring to the client computers, those are Windows 10, with perhaps one still on Windows 7.
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Commented:
powershell to enable smbv1.0 on the server2019 essential
https://techcommunity.microsoft.com/t5/windows-server-insiders/windows-server-2019-build-17623-smb1-does-no-more-exists/m-p/176832


Make sure the existing DC is set for DFSR based replication and not FRS which is not supported by the server 2019
https://techcommunity.microsoft.com/t5/storage-at-microsoft/streamlined-migration-of-frs-to-dfsr-sysvol/ba-p/425405

How are currently the computer(clients) access the shared folders, server based on domain based shares?
Does the existing fileserver (2008) includes the DFS /dfsr features enabled?
DanOwner
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Commented:
Before you do anything, I would defiantly visualize that box so if things go bad you can still have a DC in your back pocket.  You don't need to image the data, just the sys drive.
Shaun VermaakSenior Consultant
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Distinguished Expert 2019

Commented:

If you virtualize the DC for backup purposes nothing stops you from making a duplicate, offline copy of it and test the upgrade process. 

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Distinguished Expert 2019

Commented:
The asker is not going through an in-place upgrade.
The asker having a win2k8 standard DC+fileserver is now interested in deploying a new 2019 Essential server into the existing environment.
dilemma deals with AD and whether server 2019 essential can join the existing domain, get sysvol replicated, etc. and then handle the data migration .....
John AtkinsonIT Consultant

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Commented:
I’m pretty sure Win2019 Essentials can’t join another domain.  Given that, what are my options for transferring AD information?  Also, having never done a server migration, I ask, what’s the concern about replicating sysvol?
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Distinguished Expert 2019
Commented:
usually, people start with SBS/essential and upgrade. You are trying to downgrade.
The replication of sysvol is the location where hips and scripts are.

Your other option is to backup the data on the 2008 and restore it on the 2019. Note you have to preset the folders and use icacls or powershell that can reset, change security
The other using ldif export of users...and computers, or might be cleaner to setup the 2019 as a new AD to then join the client systems to the new.
John AtkinsonIT Consultant

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Commented:
Thanks, all.  I think I'll be migrating by hand.