OpenVPN (Tunnelblick) Suddenly Dropping Constantly

Posted by Jeremy Privett on Super User See other posts from Super User or by Jeremy Privett
Published on 2010-05-04T06:43:50Z Indexed on 2010/05/04 6:49 UTC
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I've been using Tunnelblick on my Mac for OpenVPN for about a year now. All of a sudden, this morning, it decided that it was going to take a nasty turn for the worse with no explanation. Here are the symptoms I'm seeing:

  • I can connect to the VPN fine, initially.
  • After about 2 - 5 minutes of no interruption, the connection suddenly dies.
  • I can still see the VPN route using netstat -rn, and Tunnelblick believes it's still connected.
  • No VPN traffic can go through and I can't even ping the VPN gateway.
  • Eventually, Tunnelblick will catch on that the connection has died (usually about 5 - 10 minutes later) and shoot itself to restart and then the cycle starts over again.

I've tried everything I can think of to figure this one out. I've completely flushed my system by rebooting and removing Tunnelblick and all traces of OpenVPN from my system and re-installing from scratch. No dice, same problem.

I'm at my wits end, because I desperately need to get this fixed as the VPN is required for me to be able to do my job. Any ideas you have would be greatly appreciated.

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