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I spent a lot of time surfing the web for the solution, but alas, so I finally concluded that this might be an interesting topic to discover.

Here's the task:

1. I need to establish VPN connection from MAC OS X (preferrably built in IPSec client) to remote Cisco ASA 5500.

2. What I have: two certificates, one for VPN connection cyphering, one for remote desktop login. Both of them stored on eToken.

The problem is in setting up the connection: On the cisco official website there is a remark about supported vpn clients and there mac os x built in IPSec client seems to be suitable. Moreover, for ASA 5500 it's suitable both in "l2tp over ipsec" and "Cisco IPSec" modes. Now, let's try to establish "Cisco IPSec" (settings>network>add connection). I have host address, account name and password, and I'm sure it's correct because I checked it in Win7.

The most interesting thing is in "Authentication settings": here, I supposed to choose a certificate, but my Keychain reports, that there are no suitable certificates in my Keychain.

And the reason for that might be in "type" of certificates. All the certificates I have are identified by OS X as a user certificates so it cannot be used to authorize the machine (by the way, is it right?).

Okay, if we try the l2tp over IPSec there is the same problem: I can even choose a user cerificate from eToken, but I still have no machine cert.

This is how it usually looks like in Windows:

  1. Run Cisco VPN Client

  2. Set up Host address, than just choose certificate (which is allowed to be choosed somehow :) )

  3. Tap connect, enter pin for eToken and you are connected

So how to set up a connection if:

1. eToken is quite visible with its certs even for native IPsec client.

2. There is a cisco asa 5500 on other end.

OR I would be glad for a hint or a link to where I can find any description about cisco vpn features...

System: OS X Lion 10.7.4, eToken SafeNet Authentication Client 8.0.

If someone know a decision for different clients - it will be nice to see it here.

Thanks beforehand!

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