Upgrading your Remote Desktop Session Host to Windows Server 2016

Applies to: Windows Server (Semi-Annual Channel), Windows Server 2019, Windows Server 2016

Important

All applications must be uninstalled before the upgrade and reinstalled after the upgrade to avoid any app compatibility issues that may rise because of the upgrade.

Supported OS upgrades with RDS role installed

Upgrades to Windows Server 2016 are supported only from Windows Server 2012 R2 and Windows Server 2016 TP5.

Upgrading a RDS session-based collection

In order to keep the down-time to a minimum, it is best to follow the steps below while upgrading a RDS session-based collection:

  1. Identify the servers to be upgraded, say, half the servers in the collection.
  2. Prevent new connections to these servers by setting Allow New Connections to false.
  3. Log off all sessions on these servers.
  4. Remove these servers from the collection.
  5. Upgrade the servers to Windows Server 2016.
  6. Set Allow New Connections to "false" on the remaining servers in the collection.
  7. Add the upgraded servers back to their corresponding collections.
  8. Remove the remaining set of servers to be upgraded from the collection.
  9. Set Allow New Connections to "true" on the upgraded servers in the collection.
  10. Now upgrade the remaining servers in the deployment by following steps 3 through 9 above.

Upgrading a standalone RD Session Host server

A standalone RD Session Host server can be upgraded anytime.