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Setting up OpenVPN on OSX

OSX:

  • Download Tunnelblick 3.0 zip file
  • Copy Tunnelblick from the zip file to your Applications folder and run it
  • Select open if you get a warning about it being downloaded from the Internet
  • You'll be prompted to enter your local system password (tunnelblick needs to run as administrator to set up routing)
  • Install may fail with an error the first time run, if it does just run Tunnelblick again.
  • To connect to the vpn click on the closed Tunnelblick icon and choose Connect 'vpn1'

  • Tunnelblick icon will turn from dark to light (closed to open) when connected.
  • Once connected all traffic should be passing through the VPN
  • Check here to verify it is. The IP and name shown should be for packetderm.com, not your ISP.

Common Issues

Below are the most common reasons helpdesk has seen for OpenVPN not working correctly on OSX, either not being able to connect or looking connected but not passing traffic (in order of most common to least):

  • Some versions of Snow Leopard do not properly handle the DHCP DNS push. If this affects you there is a fix, but it is not a "one fix fits all" and so there are some troubleshooting steps you need to take and report back to us, please contact helpdesk with a copy of your log file.

If you cannot connect to some sites (like facebook or youtube):

  • This is most often the result of either a "poisoned" DNS cache (by poisoned we mean cached blocked values from before VPN launch) or DNS leaks (see clearing your DNS cache and DNS Leaks)
  • If Snow Leopard, see listing about the DHCP DNS push not being properly handled under common issues.


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