Hey @LNeuman
May I know how are RDS roles distributed in your environment?
There is a restriction on the number of simultaneous RDP sessions – only one remote user can work at a time. If you want more than 2 concurrent connections, you will need to install the Remote Desktop Session Host (RDSH) role and buy "Remote Desktop Services client access licenses" (RDS CALs) for people to connect.
1.What is the root of this limitation to a single connection?
Please check from the group policy , whether the connections has been limited to only one user.
Configuration > Administrative Templates > Windows Components > Remote Desktop Services > Remote Desktop Session Host > limit number of Connections: set to Disabled or Not Configured
2.Remotely check whether or not a session is already in progress, without causing it to disconnect or otherwise interfering with it?
First you need to have admin rights to connect with remote server, then on the server, you can find active users in Task manager users Tab. Without connecting, I don’t think it’s possible.
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Best Regards
Karlie