I am currently running Mac OS X Snow Leopard and trying to use the native vpn client to connect to our Microsoft vpn server. If I route all traffic via the vpn connection I am able to connect to our servers, however, external traffic to i.e. google or stack overflow is blocked. If I uncheck the checkbox to route all traffic via the vpn I can connect to the vpn, however, I can not connect to my servers, external traffic to google or stackoverflow works though.
Is this a VPNclient issue, do I need to purchase Mac OS X VPN software instead of the native client, or is there a Microsoft vpn server setting that has to be checked. I am not familiar with the server software, but I wanted to post this question here to help out our network admin with the Mac OS X machines.
Update:
While I have not 100% ruled out the OS X VPN client, I have determined my router is definitely part of the issue. I have a Linksys wrt54g 1st gen, which worked perfectly for awhile, now I am guessing it has fried, because with it tied to my home network it prevents me from connected to my VPN. if i disconnect it and go directly through comcast, or any of my local coffee shops, everything works fine. once i replace the router to confirm, I was going to update this issue.
Best Answer
My guess is that this is a routing issue. Try going to System Preferences -> Network, click the Gear/configuration icon under the interface list and select "Set Service Order..." from the pop-up menu. Once in the service order sheet, drag your VPN connection to the very top, save the settings, and try again. Leave the "Send all traffic over VPN connection" setting disabled.
If this resolves the issue, it's likely because the non-VPN network you are on is trying to route the packets to 65.x.x.x as it's an interface with higher priority in the routing table and also may have a valid route to 65.x.x.x, but obviously the connection doesn't complete due to routing/firewalling further down the line. The VPN interface is likely lower in the routing table than the non-VPN network, so by pushing it up in priority (and leaving "Send all traffic over VPN connection" off) it should route the VPN traffic correctly because it has a valid & more specific route to it, but will let the remaining traffic flow normally over the non-VPN interface.