Setting Up Mac For Cisco Vpn Ipsec

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Configuring IPSec VPN on Cisco IOS. Figure A offers a simplified view of how IPSec works on a Cisco router. Two routers set up a virtual IPSec tunnel between each other using common algorithms.

I have an iMac (OSX 10.7.5) on which I have a VPN set up using Cisco IPsec. This works fine from the iMac and I can access hosts at the remote end of the VPN tunnel as expected. I'm using the VPN to access a web-based vSphere client so I can do server administration work on a VMware vCenter in another location. It seems that the web UI for working with the vSphere client requires a couple of plugins, and these plugins are not available for the iMac and OSX, only for Linux and Windows. So out of the box, the IPsec VPN does me no good.

I've had to use a Windows VM on the iMac, for which I have a Cisco VPN client, and can use the proper plugins with Firefox so I can work with the vSphere client. This runs much slower than I would like, at least as far as loading plugins (or the standalone vSphere client) is concerned.

What I would like to do is to set up the iMac so that it can act as a gateway for packets intended for the other end of the VPN, but it seems that this is easier said than done. If I could do this, I could use Firefox on a couple of Linux boxes on the LAN and set up the vSphere web access plugins on them. It's easy enough to get packets destined for the other end of the VPN to the iMac's public interface using the routing table on either one of the Linux desktop boxes, or on the Linux gateway on the LAN. The problem is that while packets to the remote host sent from the iMac via the VPN can be properly answered, packets to the same host received via the iMac's public interface are not.

Using ping and tcpdump makes this problem pretty clear. What I suspect is that the IP address of the iMac (the near end of the VPN tunnel) is duly entered into the routing tables on the far end of the tunnel by the VPN server, so replies and session traffic are properly routed back through the tunnel - and packets sent through the tunnel from other IP addresses on the LAN are dropped on the floor on the far end since their source addresses are unknown on the far end of the tunnel.

This is a classic job for network address translation, and should be simple to set up, and probably would be using Linux and iptables. It's not at all easy or obvious on the iMac! I've tried setting up Sharing for the network VPN interface, but this crashes the preconfigured address for the public LAN interface, and if I manually reset the IP address for the LAN IF, the VPN quits! Rock and a hard place, that! A bit of research turns up reports that other people have had similar problems and it seems that using interface 'Sharing' from the System Preferences dialog won't work.

Working from the CLI is dicey since there's no interface that seems to be explicitly associated with the Cisco IPsec tunnel. Excel not updating formulas automatically. Attaching tcpdump to utun0 shows nothing about traffic through the tunnel. I've had this problem with IPsec installations before.

They just work (if they work at all) but you can't do much by way of routing which requires an interface spec because the real interface is apparently implicit. So I'd like to at least try doing source address NAT on the iMac for packets arriving from elsewhere on my LAN, and destined for addresses on the other end of the VPN. How can I set this up? I've tried icefloor, but I'm getting obscure error messages from it.