Some time ago I wrote a post on how to get a Cisco IP-Sec VPN working with client certificates on OS-X Lion. Now I upgraded to Mavericks and of course this broke my VPN connection again. Fortunately a friend already had the same problem on Mountain Lion and his fix also worked on Mavericks. To get my connections working on Mavericks I followed the instructions from my previous post: . After that I had to “allow all applications to access this item” on the certificate in Keychain.

Also see the last comment in saying to allow all access to the cert in Keychain.

I had already set the cert to be always “Trusted” but you have to expand the cert to get to the private key and always “Allow” access to it. It’s a different setting.

See the screenshot below.
VPN cert