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Given that OS X now supports (natively) CISCO IPSec VPN connections I am wondering what the requirements for the VPN configuration are on the remote end?

I have evaluated a number of CISCO devices (in the smaller range, such as the ASA 5505 routers, as well as the RV120W and the WRVS4400N devices) and haven't had a lot of luck getting them to talk to the VPN via the built in Client, however when I use something such as IPSecuritas from Lobotomo I am able to establish a connection without any issues.

So what is the ideal configuration to get this working? I would honestly prefer to not have to install a VPN client on my systems and simply use the built in client.

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Any log entries on the ASA when the connection attempt fails? – Shane Madden Oct 20 '11 at 16:34

3 Answers 3

Since Apple claims that Cisco VPN is natively supported, and it is explained in detail here, my guess would be a VPN configuration issue or mismatch.

It may be a matter of matching the Remote Access VPN setup to the OSX client, instead of the other way around.

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From my experience, you will have to create a group on the ASA and assign it a password. You then add the user to this group.

In OSX, the account name and password is of the user's. Then under "Authentication Settings" type in the password (shared secret) for the group you configured on the ASA and type in the name of the group in the "Group Name" field.

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I've copied and pasted what I hope is the relevant config out of my ASA (5525) where this is working for both AnyConnect and MacOS-native clients. I have expurgated it of localized information, so I may have typoed something along the way. I hope I haven't left anything out. (Look out for ! *** comments.)

! *** This is a pool of IPs that will be allocated to VPN clients
ip local pool Pool_VPN mask
! *** These are the networks accessible via the VPN
access-list Split_Tunnel standard permit
access-list Split_Tunnel standard permit
access-list Split_Tunnel standard permit
 ! *** See below for the content of this file
 anyconnect profiles ExampleVPN disk0:/examplevpn.xml
group-policy GP_VPN internal
group-policy GP_VPN attributes
 wins-server none
 ! *** Replace with your internal DNS server
 dns-server value
 vpn-tunnel-protocol ikev1 ikev2 l2tp-ipsec ssl-client ssl-clientless
 password-storage enable
 group-lock value TG_VPN
 split-tunnel-policy tunnelspecified
 ipv6-split-tunnel-policy tunnelspecified
 split-tunnel-network-list value Split_Tunnel
 ! *** Replace with your internal DNS zone
 default-domain value
 split-dns none
 split-tunnel-all-dns disable
 secure-unit-authentication disable
 ! *** Replace with the FQDN of your ASA
 gateway-fqdn value
 address-pools value Pool_VPN
 client-access-rule none
  anyconnect profiles value ExampleVPN type user
  anyconnect ask none default anyconnect
tunnel-group TG_VPN type remote-access
tunnel-group TG_VPN general-attributes
 address-pool Pool_VPN
 default-group-policy GP_VPN
tunnel-group TG_VPN webvpn-attributes
 group-alias TG_VPN enable
tunnel-group TG_VPN ipsec-attributes
 ! *** Replace with your own shared secret
 ikev1 pre-shared-key ThisIsASharedSecret
tunnel-group-map default-group IPSecProfile

The file disk0:/examplevpn.xml contains:

<AnyConnectProfile xmlns="">

Replace with the external FQDN and IP address of your ASA.

Then set up your MacOS "Cisco IPSec" client to use the same shared secret as is found in the "ikev1 pre-shared-key" line and the group name is the tunnel-group, in this case "TG_VPN". The username and password are locally defined in the ASA with lines like:

username user password ***** encrypted privilege 15

I'm guessing it's using the local accounts as a result of:

user-identity default-domain LOCAL

But if you can get this working with local users, you can probably work to get auth set up differently if you need.

I will say that I started with an already-working AnyConnect config and then just added these lines:

tunnel-group TG_VPN ipsec-attributes
 ikev1 pre-shared-key ThisIsASharedSecret

to get it to work with the MacOS client. (I also had to expand the split tunnel network access list, but I suspect that that was needed for the AnyConnect users, too.)

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