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Upgrading Windows 2012R2 to Windows 2019

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Last Modified: 2020-02-19
Hi,
 
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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