RDP Disconnects After Connecting Through an SSH Tunnel in VMware Workstation

The SSH tunnel looked fine. I could connect to the Windows 11 Pro guest, start an RDP session, and then watch it drop again a short time later. It was the kind of failure that invites a long detour into SSH settings, even though SSH was not the part falling over.

The setup was VMware Workstation on Windows. An Ubuntu Server VM provided the SSH tunnel, and the Windows 11 Pro VM was the RDP target. The tunnel was already established by the time the remote desktop client connected, so this was not an authentication problem or a tunnel that never came up.

What made the problem confusing

The connection sequence gave every sign of working. The local forwarded port accepted the connection, the RDP login screen appeared, and a session could start. The failure came afterward: the session disconnected while it was in use.

That detail rules out a lot of the usual first guesses. If the tunnel configuration were simply wrong, the RDP client would normally fail to reach the guest at all. Here, it reached the guest and then lost a connection that had already been established.

I retried the same path enough times to treat it as a pattern rather than a one-off Windows hiccup. The result was the same: an RDP session through the Ubuntu SSH tunnel was not stable inside this VMware Workstation environment.

Where the fault appears to be

The weak point was VMware Workstation’s virtual networking path for this particular RDP-over-SSH arrangement. It could carry the initial connection, but it could not keep the session reliable.

That is an important distinction when troubleshooting. Changing the Ubuntu Server configuration, recreating the SSH tunnel, or focusing on RDP credentials does not fix the component that is behaving badly. The tunnel has already done its job before the disconnect happens.

This is not a claim that every RDP connection in VMware Workstation fails, nor that SSH tunnelling is generally unreliable. It is a practical conclusion from this setup: Windows 11 Pro RDP through an Ubuntu Server SSH tunnel repeatedly disconnected, and the virtual networking layer was the common factor.

A sensible way to test it

Before changing more settings, confirm the symptom in a small, repeatable test:

• Start the Ubuntu Server VM and establish the SSH tunnel.
• Connect to the Windows 11 Pro VM through the forwarded local port.
• Keep the RDP session open long enough to see whether it remains usable.
• Repeat the test after restarting the virtual machines, rather than assuming a single successful connection proves the path is stable.

It is also useful to compare a direct RDP connection on the same network path, if that is available. A direct connection that stays up while the tunnelled connection drops is stronger evidence that the combination of virtual networking and the tunnelled path deserves attention.

What I would do instead

I would not use this VMware Workstation setup for work that depends on a stable RDP session. A remote desktop session that opens reliably but disconnects later is especially disruptive because it can appear fixed until work is already underway.

Use a different virtualization or remote-access route for the Windows guest, or move the workload to a host where the network path is known to stay up. That is less satisfying than finding one checkbox to change, but it is the practical answer when the application itself is the unstable part of the stack.

The lesson here is to separate “can connect” from “can stay connected.” In this case, the first one worked; the second one did not.