My Windows PC can connect without problems to a Windows Server 2008 VPN at my office. Everything works.

I set up the same VPN in my Mac with Snow Leopard. It connects, but I can't access any remote computer inside office's VPN.

I have played with some VPN settings, but without success.


  • Did you find a solution? – sclarson Dec 21 '09 at 17:26
  • Oh yes, please let's restart it. I tried to connect a MacBook Air to a MS VPN without success. The connection should be authenticated with certificates. I had success with Cisco VPN, but that is about to be replaced with the MS VPN. So, what do I need therefore? Can it be done with the MacOSX built in VPN client (preferred), or do I need a software like IPSecuritas? Which information do I need to enter? It is a very large MS network (AD, Kerberos) what should be connected to. I am Mac related, left-handed with MS. ;-) – user72179 Feb 25 '11 at 12:00
  • already tried to use the IP address of the server?
  • double checked routing settings on your mac?
  • tried to check the "send all traffic over VNP"
  • remote IP address range conflicts with the local one? (routing problems again)
  • * IP doesn't work. * How can I check the routing settings on my mac? I'm very new to mac world. * Tried, but didn't help. – Erick Sasse Oct 16 '09 at 0:50

When VPN'd in from your mac could you run the following commands from a terminal and give us the output:

sudo ifconfig

sudo route

When VPN'd in on your windows machine could you give the output of the following 2 commands and give us the output:

ipconfig /all

route print

Comparing these will show if you have similar routing when connected on each device and ensure that you are getting a correct IP on your mac like you are on your PC. My initial suspicion is that you are not getting a correct default gateway update or route update on your mac like you are on your PC. This was too long to coherently put as a comment.

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