Move to Windows Server 2016 or Straight to 2019

[WarnerK]

To collect your info
Open a command prompt, go to c:\Windows\system32, and then type systeminfo.exe.

Copy, paste, and store the resulting system information somewhere off of your device.

Type ipconfig /all into the command prompt, and then copy and paste the resulting configuration information into the same location as above.

Open the Registry Editor, go to the HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\Windows NT\CurrentVersion key, and then copy and paste the Windows Server BuildLabEx (version) and EditionID (edition) into the same location as above.

To perform the upgrade
Make sure the BuildLabEx value says you're running Windows Server 2016.

Locate the Windows Server 2019 Setup media, and then select setup.exe.

Select Yes to start the setup process.

For internet-connected devices, select the Download updates, drivers and optional features (recommended) option, and then select Next.

Setup checks your device configuration, you must wait for it to finish, and then select Next.

Depending on the distribution channel that you received Windows Server media from (Retail, Volume License, OEM, ODM, etc.) and the license for the server, you may be prompted to enter a licensing key to continue.

Select the Windows Server 2019 edition you want to install, and then select Next.

Select Accept to accept the terms of your licensing agreement, based on your distribution channel (such as, Retail, Volume License, OEM, ODM, and so on).

Select Keep personal files and apps to choose to do an in-place upgrade, and then select Next.

After Setup analyzes your device, it will prompt you to proceed with your upgrade by selecting Install.


To make sure your upgrade was successful
Open the Registry Editor, go to the HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\Windows NT\CurrentVersion key, and view the ProductName. You should see your edition of Windows Server 2019, for example Windows Server 2019 Datacenter.

Make sure all of your applications are running and that your client connections to the applications are successful.

[Akshay_M]

2016 and 2019 aren't as massively different as say 08 and 12 were. Even the jump from 12R2 to 16 wasn't as bad as I initially thought but there are some pain points.

there are some technet articles about removed features/no longer being developed features for each OS you should check out, but they're fairly minimal.


Regards,
Akshay

[saviogomes]

I'm the IT manager for a small company and we're currently running a couple of dozen Windows Server 2012R2 Standard servers. We have software assurance and I would like to make the move up to 2016 but 2019 is out already. Generally, we've stayed 1 version back from current (we upgraded to 2012 R2 when 2016 came out) and I don't see any need to be on the bleeding edge but I'm wondering if there is any big reason to go straight to 2019.