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Short Question
Is there something I am missing when setting up a Cisco IPSec VPN connection that redirects all traffic over the VPN?

When I am connected to the VPN, I can browse our company's intranet with no problems, but when I try to go out to say it times out. Another co-worker is having the same problem on his MBP as well. The VPN client we use for our Windows machines is Shrew Soft talking to a pfSense router, which works like a champ.

System Information
MBP early 2008
4GB Ram
500GB 7200RPM HDD

OS X 10.6.8
Bootcamp and Parallels 6: Windows 7 Pro

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You are looking for what is known as split-tunneling. Basically what that means is that any traffic not bound for the VPN's network stays local, and is routed through your default gateway. That said, some VPN's force you to use their gateway, and if it is not configured to let you browse the Internet, you cannot do anything. I do not know that VPN client unless I see it, so I cannot guide you more. – KCotreau Jul 15 '11 at 2:34
@KCotreau: If it is the actual client side, wouldn't this problem be on both Windows and Mac? Windows is still able to use my internet connection for normal traffic. This is why I feel it's something up with my Mac's VPN settings. Thanks for the quick comment tho ! – Adam Lewis Jul 15 '11 at 2:37
Your comment does make me think one thing: They are not forcing settings like not allowing split tunneling. Yes, I believe your Mac VPN client is mis-configured. I don't know what the setting it, but it is probably related to what I mentioned before, split tunneling. Based on how I described it, you can do one of four things: Try to figure it out yourself, ask your IT dept about it and mention split tunneling, or post screenshots of all your VPN settings. You can blur the info, but I could probably figure it out if I could see it. The forth thing: Hope someone else here knows more than me. – KCotreau Jul 15 '11 at 2:55

I had the same problem once, except for accessing the internal intranet (I couldn't access ANYTHING, but I didn't have something running in the same network to try). I used the VPN to hit a remote API.

The problem was related to DNS servers. I can't tell you exactly where it was because I left the MacBook at the office and I use Linux at home.

But the VPN configuration tool assumed that you needed a different set of DNS servers and I can't remember if it was empty or if it defaulted to something invalid.

I just used (Google's DNS servers) and it started working.

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I tried switching DNS servers with no luck. It really is an issue with split tunneling. – Adam Lewis Aug 30 '11 at 15:20
up vote 0 down vote accepted

We were able to resolve this issue by running Shrewsoft's 2.2 Beta release that supports Mac OS X. The install directions are here. So far this seems to be working like a champ. It also allows a single configuration for both Windows and Mac users regarding the VPN configuration.

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