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VPN fails to restart after sleep

I use the built-in VPN in OSX 10.6.5. Now and then, after laptop has been to sleep mode, VPN fails to restart ("Configuration error. Check settings and try to reconnect."). The only solution is to restart my laptop. Is there a fix for this? If not, can I restart the built-in VPN in a terminal window (instead of restarting my laptop)?

MacBookPro 13", Mac OS X (10.6.5)

Posted on Dec 30, 2010 5:45 AM

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22 replies

May 8, 2011 1:50 AM in response to jvdesomp

I also have the same problem on 10.6.7 and restarting the racoon services does not solve the issue for me. I am on wired Ethernet. The only option I have is to restart the operating system. I have been using the in built Cisco VPN client for over three years and this has always been a problem. The same problem is a lot worse on my Mac Air where I am using wireless. On the Mac Air I get other problems like the finder hanging while trying to re-connect to an SMB share after waking it up out of sleep mode - this is without the VPN using WiFi in the office. Perhaps there is a general problem with OS X recovering its network state after being in sleep mode.


Come on Apple, your better than this...

Jun 5, 2012 7:27 AM in response to jvdesomp

I can almost entirely avoid this problem by ensuring that my VPN is disconnected prior to sleeping the system. I do, however, often have this problem on flaky network connectsion (such as hotel conference rooms). Truly annoying in an otherwise great experience. This is the primary reason I have to reboot my mac.


However (there's always a however), I am on a corporate mac, and do not have root access. Any suggestions on how to reset racooon without being able to sudo?

Jan 24, 2013 4:28 AM in response to jvdesomp

I have this problem when I forget to disconnect a VPN connection before I shut down my iMac. When I wake it up again in the morning there will be a warning that my VPN connection was lost. After that I cannot reconnect the VPN and Safari, Chrome and Firefox all say I'm not connected to the Internet and Mail is offline. But 'Network Diagnostics' says everything is working and I can ping domain names in Terminal and resolve addresses, Filezilla will even connect to FTP sites, DropBox will update files and DHCP works.


It is very annoying having to reboot and reload everything that was open the night before.


For me stopping/starting the racoon service fixes the VPN problem but doesn't help with Safari etc and my only recourse is to reboot the machine. Restarting the Finder doesn't help either.


OSX 10.6.8 Core i5 iMac

Ethernet Cable connection or wifi

VPN fails to restart after sleep

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