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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.

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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)



using ipfw (on OS X Snow Leopard and older)



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.

all of my content is released under CC-BY-SA 2.0

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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.

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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!!

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