First RDP launch sometimes does not establish the SSH tunnel connection, second launch works

Hi,

I'm experiencing an issue when using an SSH Tunnel configured as the VPN for an RDP session.

The VPN (SSH tunnel) is configured on the folder and inherited by the RDP entry.

Sometimes the first attempt to open the RDP session does not establish a connection. The RDP client stays in the initialization phase and eventually times out. If I close both the RDP session and the SSH tunnel, then launch the exact same RDP entry again (which recreates the SSH tunnel automatically), it connects successfully.

Here are my observations:

• I can confirm that the SSH tunnel itself is fully established before the RDP client is launched.
• The RDP client definitely attempts to connect to a localhost port, as expected when using the SSH tunnel.
• However, when the first attempt does not succeed, I can see in the SSH logs that the connection request for the destination host is never initiated. In other words, the SSH server never receives the request to open the forwarded connection for the RDP destination.
• On the second attempt, the SSH tunnel behaves as expected: the forwarded connection request is triggered, the SSH server opens the connection to the destination host, and the RDP session connects successfully.
• The SSH Tunnel VPN settings are configured with Use over a secure gateway, and Use dynamic port.

From what I can see, this doesn't appear to be an issue with the SSH tunnel failing to establish. Instead, it looks as though the first RDP launch sometimes doesn't trigger the forwarded connection through the existing tunnel, even though the RDP client is connecting to the local forwarded port.

Has anyone experienced something similar, or is this a known issue? Are there any additional RDM logs that would help determine why the first RDP launch doesn't appear to initiate the forwarded connection through the SSH tunnel?

Thanks!