Upgrade from Windows server 2016 to Windows Server 2019

Occasional Contributor


When Windows Server 2019 will be RTM later these year can upgrade my Windows Server 2016 to that new server or must do clean installation have an genuine product key for Windows Server 2016.

9 Replies
best response confirmed by John Marlin (Microsoft)

We have been working hard improving the in-place upgrade experience in Windows Server 2019.  Yes, you are able to do an in-place upgrade of either Windows 2012 R2 or 2016 to Windows Server 2019.

Thanks for info, will there be an version for Essential then Windows Server 2019 going to RTM later these year!

Hey again, must buy an new product key when upgrade my Windows Server 2016 Essentials when Windows Server 2019 going to RTM later these year!!

See articles linked below.  Microsoft is pretty much killing off what made Server Essentials 2012 and 2016 such great products for small business customers.  The Essentials Role is dead, it is NOT going to be in Windows Server 2019 Essentials, Standard, or Datacenter.  Terrible news for my customers and my business! 



Good to know. Also if im in windows server 2019 preview will i be able to upgrade to 2019?

Thanks for your comment John. In some moments I will be upgrading my RDS 2016 template based on Windows Server 2016 to Windows Server 2019. I am looking for to have this smooth as my RDS template took me some time to be prepared.


As Windows Server 2016 doesn't support native OneDrive client I am really looking forward to have this working with 2019 version and utilizing the On-Demand feature. Current there is a logon script for OneDrive Mapper powershell that utilizes the WebDAV virtual mapping. I don't like this solution, it makes the redirected folders slow and prone for logon issues due to various scripts are needed.

Currently in place upgrade is not working from windows server 2016 full (not preview) to windows server 2019 (full not preview) I have licences.


When I try to upgrade I get and error : not current version go to KB4464619 however when I go there nothing and no windows update finds it either


Any solutions???

KB4464619 is not an installable update, it is an informational about why an in-place upgrade may be blocked.




Greetings @Jonathan OBrien Just an FYI to the MS Community. Within the Test Out Lab Sim for Network Pro and the Networking Operating course, the simulations for configuring and IP times out while using is trouble-shooting. It appears as though the DHCP Server option within Tools and the drop down menu of the Server Management does not appear and times out after 23 minutes. Happy testing!


Kind Regards,