You mentioned to keep the SSH-Session open to be able to tunneldata to
your proxy. I personaly think that`s sub-optimal.

A better solution would be to use the Multiplexing feature of OpenSSH
combined with Port-Forwarding.

PROXY is defined in /etc/hosts

ssh -f -C -N -L 8080:PROXY:8080 PROXY
ssh -f -C -N -L 10025:PROXY:25 PROXY
ssh -f -C -N -L 10110:PROXY:110 PROXY
ssh -f -C -N -L 6667:PROXY:6667 PROXY

This would tunnel serval Ports to PROXY.
You should use Localports higher then 1024 because a normal user donīt
own the rights to bind anything to Ports below 1024.

Well but even this solution is not optimal because you would etablish 4
different Connections to PROXY.

If you apply this to the ~/.ssh/config you do create a multiplexed
connection:

HOST *
Controlmaster auto
ControlPath ~/.ssh/ssh-ControlSocket-%r@%h:%p

This would create always a multiplexd connection for any Host if no
Controlmaster runs. If a multiplexed connection does already exists
it`s used to Login/Tunnel/Whatever.


I hope you`ve found this usefull because it would be correct in my oppinion.


Kind regards,
Rembrandt