No more annoying password popups for Cisco VPN on OSX Lion (and Mountain Lion)!

I am currently working on a development project for our office in München. Accessing their internal servers requires connection via VPN (I’m working from Stockholm). I’m using the very handy built-in Cisco IPSEC VPN client in OSX and have had some annoying problems which until today I have not been able to solve. I am documenting these configuration changes so I remember what I did, and hopefully it can also help others out there!

The problem

After being connected via VPN for about 48-54 minutes (seems to vary), OSX will throw up a “please enter password” dialog (I can’t remember the exact wording…). After entering the password, the VPN connection stays active for another 48-54 minutes, at which time another password dialog pops up. Lather, rinse, repeat. Not very fun during a standard work day, especially when my application-in-progress likes to crap out as soon as it loses connectivity to those remote servers (and requires lengthy restarts).

The solution (I thought)

After much googling I found this solution, for which I had high hopes (despite the comments from fellow OSX Lion users who couldn’t get the solution to work). In short, that post goes about showing how to grant /usr/libexec/configd access to your keychain, in order to squelch the password dialog. Well, unfortunately that solution didn’t work for me as well 😦

The working solution (finally!)

After a week or so of still getting that annoying password dialog, I managed to google the correct sequence of terms and I finally found a working solution! Over at the Apple forums, a very clever Mr Geordiadis posts a working solution to the problem. His solution is to modify the racoon configuration files for the VPN connection by tweaking a few settings and increasing the negotiated password timeout value from 3600 seconds to 24 hours (perfectly fine for my intended use). I’ve been connected now for over 8 hours today, haven’t had a password dialog yet! So excellent! Confirmed that it works on Mountain Lion (10.8) as well.

I hope this information helps you as it helped me!


  • Connect to the VPN so the configuration file is generated
  • Create a location for the VPN configuration files

    $ sudo mkdir /etc/racoon/vpn
  • Copy the auto-generated configuration file into the new configuration folder:

    $ sudo cp /var/run/racoon/ /etc/racoon/vpn/
  • Edit the racoon.conf file:

    $ sudo emacs /etc/racoon/racoon.conf
  • Comment out the include line at the end of the file and include the new configuration folder:

    #include "/var/run/racoon/*.conf" ;
    include "/etc/racoon/vpn/*.conf" ;
  • Edit the VPN configuration file:

    $ sudo emacs /etc/racoon/vpn/
    • Disable dead peer detection:

      dpd_delay 0;
    • Change proposal check to claim from obey:

      proposal_check claim;
    • Change the proposed lifetime in each proposal (24 hours instead of 3600 seconds):

      lifetime time 24 hours;
  • Disconnect VPN and reconnect.

Updated 2012-08-07: added the detailed steps
Updated 2012-08-07: tested on OSX Mountain Lion (10.8)


  1. Greg

    Hi. Love this solution. It’s the only thing that I found to work. One caveat is that the file in /etc/racoon/vpn/ needs to be updated when the IP address of the VPN server changes. I have a my VPN behind a dynamic IP address and use DynDNS to keep it updated. When the IP does change, the configuration file is no longer valid and will not let me connect to the VPN. Once I repeat these steps, my computer connects up to my VPN again. Thanks again for the solution.

    • David

      I can’t take credit for the solution, and yes the filename changes if the server IP changes which can be a bit annoying… but glad it works for you!

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s