First of all, thank you very much for the extensive help.
Short inventory of our environment :
We have 14 virtual machines (Windows 10) configured as jump hosts, to set up VPN connections to our customers.
These VPN connections can be of any kind, any client (Cisco, SonicWall, Citrix, etc).
These VPN clients are all installed on the virtual machines.
When I set up an entry, using VPN of any kind, I make sure that I am able to manually connect to the customer using the VPN client itself.
Secondly I add the RDP session to the customers's server and test it again.
Once that is working correctly, last change I make is set up the jump to the correct jump server/virtual machine.
Even then I test the connection.
If it works, I move the session entry to another folder within RDM to be visible to our agents/consultants.
Mind you that I have RDM in autostart on the virtual machines/jump hosts AND RDMagent starts automatically.
Each consultants who uses the jump host, will get RDM opening automatically and RDMagent starting automatically.
I have done what you asked me and tested even a little further.
This time I left RDM open on the jump host and simply disconnected, so my session is still there.
From my laptop I started the session entry. It jumped again to the jump host.....and it started the session correctly.
Then I completely logged of the jump host and started again the same session....this time it jumped but wouldn't start the session.
So I have 2 sessions : first one at 15:45:24 where I start the session to the jump host picking up my disconnected session --> it worked
Second one was at 15:46:45 where I started from scratch, making the jump, started RDM automatically but it didn't pick up the session.
System.Threading.ThreadAbortException: De thread is afgebroken. (translated : the thread is disconnected)
bij System.Threading.ExecutionContext.RunInternal(ExecutionContext executionContext, ContextCallback callback, Object state, Boolean preserveSyncCtx)
bij System.Threading.ExecutionContext.Run(ExecutionContext executionContext, ContextCallback callback, Object state, Boolean preserveSyncCtx)
bij System.Threading.ExecutionContext.Run(ExecutionContext executionContext, ContextCallback callback, Object state)
I really hope you have a solution for this.