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Upgrading Windows 2012R2 to Windows 2019

I have a Stand-alone Windows 2012R2 server with 8 users. it has two drive letters: C (OS & business software) and E (User Files).  Current server is domain controller, file and print server (one big office copier/scanner/fax) and runs  Remote Desktop gateway service (there are two users who connect to their office PCs from home).

I have a new replacement the server loaded with Windows Server 2019 running Hyper-V  and am considering two options:

(1) In-Place Upgrade:
 -  Create a vhdx file from W2012R2 server using Disk2VHD and use it as existing hard drive in new virtual machine. Start the W2012R2 VM and assign static IP address. After making sure that W2012 VM is running like when it was in a stand-alone server environment, I would  change Image file to Windows2019.ISO file in Settings, Copy Windows Server 2019 setup files to a temporary folder, run Setup.exe and choose "Keep personal files and apps" option.  All Done!

(2) Create two VMs
 - First VM will be domain controller, print server and runs remote desktop gateway service . Join this VM to existing domain, transfer Master FSMO roles from current server to this new VM. Import/export printer registry and DHCP . Add remote desktop gateway service, create new Certificate and install it in user's home computers.
 - Second VM would have user files and folders and run business specific software. Install Business software. Copy Files and Folders and import Share registry from old server.
 - Demote old server and turn it off.

For simplicity, I like to go with In-Place Upgrade.
But I like to ask experts how they determine whether to perform "Simple" In-Place Upgrade or Create VMs and go thru typical new serve setup process.

Thank you for your thoughts in advance.
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Seth Simmons
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Current server is domain controller...

definitely would not do an in-place upgrade
build another server first as a second domain controller; too much of a risk if something goes wrong
second option is much safer
Avatar of CompProbSolv
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Hello There

The first option seems to be simple and much faster. True. Safer? Not at all. Things can go wrong really fast. It can bring more headaches than it's worth. I would never go this way on DC at all. If possible, a fresh installation is always better. Not only EE experts would agree, I think most of the experts would tell you the same thing. Going from 2016 to 2019 - in some circumstances, it might be a way but not from 2012 to 2019. It's too risky.
When you copy the files over (assuming you don't go with DFS), I would use robocopy and include /copy:datso and /dcopy:dat .  That will make re-sharing somewhat easier.

Keep in mind also that if you are trying to do this on the same server, it can be a bit tricky.  I'd use a Windows 10 computer to set up the two VMs.  When they are working and tested, then I'd do the clean installation of Server 2019 on your server, set up Hyper-V on it, then move the two VMs over.  Moving the VMs is very straightforward.

Alternatively, you could try to turn the 2012R2 installation into a VM, but I've found that to often be a challenge.  I would prefer to skip that step.
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"When you copy the files over (assuming you don't go with DFS)" ---> Correct. There is no DFS set up on this network.

"I would use robocopy and include /copy:datso and /dcopy:dat .  That will make re-sharing somewhat easier." -->
If I use "ROBOCOPY Source Destination /copy:datso and /dcopy:dat" comand to copy files and folders from old server to a new server, do it replace the following steps?

1. Run Regedit.msc
2. Go to  HKEY_LOCAL_MACHINE\SYSTEM\CurrentControlSet\Services\LanmanServer\Shares
3. Export the registry key
4. Go to new server and Import the registry key.

or I have to run your Robocopy command and do registry export and import?
I'm not familiar with that process of exporting and importing the key.  Let's hope someone who is familiar will give you an answer.

I usually don't have so many shares that recreating them is very difficult.  It is often a good opportunity to revisit what is shared and with whom.
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Thanks for your suggestions. I will go with new installation instead of in-place upgrade.

Also, special thanks to CompProbSolv talking about  DFS idea. I am going to try that option in  future server setup.