Windows Server 2019

Windows Server 2019 is the server counterpart of Windows 10 October 2018 Update, originally released on 2 October 2018, but was pulled due to a major bug during upgrading and was re-released on 13 November 2018. It succeeds Windows Server 2016 in the long-term servicing channel, while the semi-annual channel release of Windows Server 2019 is branded as Windows Server, version 1809 and is the successor to version 1803. It was succeeded in the long-term servicing channel by Windows Server 2022 on 18 August 2021.

It is the last version of Windows Server to have the Essentials SKU first introduced with Windows Server 2012 as Microsoft ceased further development of Windows Server Essentials after the release of Windows Server 2019 in favor of Microsoft 365. Starting with Windows Server 2022, the Essentials edition is only available to purchase from OEMs however, there is no specific installation media or SKU as the included product key instead activates the Standard edition.

It is also the last version of Windows Server to have the free Hyper-V Server SKU first introduced with Windows Server 2008 as it was replaced by the subscription-based Azure Stack HCI SKU starting with Windows Server 2022.

Windows Server 2019 drops the ability to upgrade from versions prior to Windows Server 2016.