auto init tunnel based on connectivity?

This is really beyond the scope of the client control. What you are proposing could more than likely be done in several ways (a hidden program at startup, a system service, etc). There needs to be a controlling process to manage the policy you would like to enforce. You'll also have to determine if this is to be a manual process (client provides username/password) or automatic (where the credentials are hidden securely on the machine).

 

 

Please keep in touch as I'd be very excited to hear about how you decided to implement this.

 

 

-Joe