How to enable Remote Desktop Protocol for Administration Purposes on Newly Created Windows 2019 Server

TL;DR Guide

1. Start
2. Server Manager
3. Local Server
4. Remote Desktop is disabled
5. Click Enable
6. Click Ok when prompted about firewall stuff. It automagically just adds the rules
7. Done

Once you’ve done this you probably want to enable that second user who needs to also do administration. Do this:

Start / gpedit.msc

Go to Computer Configuration > Administrative Templates > Windows Components > Remote Desktop Services > Remote Desktop Session Host > Connections. Set Restrict Remote Desktop Services user to a single Remote Desktop Services session to Disabled.

Double click Limit number of connections and set the  Maximum Connections allowed to 999999.

Please note you’ll still only have two connections and you will need proper RDS licenses to have more than 2.

Sometimes it’s also neccesary to run the command below:

gpupdate /force

Reference

• https://kb.vmware.com/s/article/81353
• https://www.layerstack.com/resources/tutorials/How-to-Enable-and-Disable-Remote-Desktop-Protocol-on-Windows-Cloud-Servers
• https://help.matrix42.com/020_ESM/MyWorkspace/10MyWorkspace_Guide/HowTo%3A_Enable_multiple_sessions_for_Remote_Desktop_Services