Tor over VPN

[anon1 0]

Sometimes I run Tor over the VPN.  If Tor leaks my IP address, will it be for the VPN server I'm connecting to, or my real IP address?  If it matters I use OS X and Viscosity for the VPN client.

[InactiveUser 188]

As long as you're connected to the VPN, any "Tor leaks" would expose your VPN's IP, not your own. 

 

You might also find it worthwile to create a firewall rule set to prohibit any connections should your VPN connection drop, or if you forget to enable it.

User jessez has provided good advice for OS X users:

 

using pf (on OS X Lion and newer)

https://airvpn.org/topic/1713-win-mac-bsd-block-traffic-when-vpn-disconnects/page-2?do=findComment&comment=2532

 

using ipfw (on OS X Snow Leopard and older)

https://airvpn.org/topic/1713-win-mac-bsd-block-traffic-when-vpn-disconnects/page-3?do=findComment&comment=2756

 

Provided you set it up correctly (test it!) and don’t get infected by root-privileged malware (which would be able to disable your firewall), nothing could get around the VPN tunnel, no matter if you're currently connected to the VPN or not.

[retiredpilot 6]

Could use direction here.  I have a machine running on Air with it locked down using all the forum firewall rules.  I just downloaded Whonix and VB.  Appeared to install easily.  I imported both the appliance VM's from Whonix.  When I fire up the gateway VM I can't get a connection.  Both theVM's stall at around 25% and whonixcheck/armwrapper, etc... just show no connection to TOR.

 

Since my host OS is locked to using only Air DNS for resolution/connecting is that a problem while trying to use Whonix?  I am somewhat confused about how to get Whonix going but at the same time make sure my ISP doesn't see any leaks through the Air tunnel.

 

Can someone give me a nudge on where to proceed?  Please.

[retiredpilot 6]

Its working now.  I shut it all down and brought it back up.  Working fine now.  I have alot to learn with the dual VM approach.  Making a post on it now!!