[kwlug-disc] Initiating connections to OpenVPN clients

Paul Nijjar paul_nijjar at yahoo.ca
Wed Jun 29 18:37:43 EDT 2011

Let's say I have the following: 

- a network named "A", which is an OpenVPN server (running on pfSense,
  as usual)
- a server named "B" on that network. It is running Windows. 
- a client named "C", which has a connection to network A. It is
  running Ubuntu, and has SSHD running on it. 

Client C can see network A. It can make arbitrary connections to
machines in that network, including server B.

However, server B cannot initiate an SSH session on C (or ping it, or
anything else). It can *respond* to requests for client C, but cannot
*initiate* anything. 

My inclination is to say that the firewall in front of client C is
blocking incoming connections from network A. But I don't know whether
OpenVPN can do magic to get around that. Can it?

My eventual goal is to initiate an SSH session from server B to client
C. (Yes, I know this is weird.) Can I do this without installing
Cygwin and SSHD on server B?

- Paul


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