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I am trying to get a mac (10.8) to connect to thru vpn to a server running Windows Server 2008 R2 pass all requests from the mac to the server.

The VPN is setup and I can connect and access the server thru a web browser, but for all other sites, the DNS lookup fails.

I have tried adding a DNS server to the VPN Host.

ex.

Lets say the the VPN server also hosts a website example.com.

I connect to the VPN with my mac and point a browser to example.com and everything works fine.

but when I point the browser to google.com it just sits there and will eventually come back with a DNS lookup failed message.

HOWEVER: I tried running the command dig @myServersIpHere www.google.com. on the mac and it comes back with correct IP addresses.

I really dont know what to do from here.

How can I route all requests from my mac, thru my windows server via VPN?

--EDIT--

Ok, stupid move of me, I changed some ips arround. The browser still tells me that dns lookups are failing, but NSlookup actually worked.

this time it produced the response of

Adam-Schiavones-MacBook-Pro:~ adam$ nslookup www.google.com
Server:     11.0.0.1
Address:    11.0.0.1#53

Non-authoritative answer:
www.google.com  canonical name = www.l.google.com.
Name:   www.l.google.com
Address: 173.194.75.106
Name:   www.l.google.com
Address: 173.194.75.99
Name:   www.l.google.com
Address: 173.194.75.105
Name:   www.l.google.com
Address: 173.194.75.147
Name:   www.l.google.com
Address: 173.194.75.104
Name:   www.l.google.com
Address: 173.194.75.103
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Is the VPN server (or rather the DNS on the server-side of the VPN) setup to forward external DNS requests? When you are connected to the VPN and run NSLookup, which DNS server is it showing? –  Ƭᴇcʜιᴇ007 Aug 29 '12 at 22:40
    
@techie007 Ok, see the edit above. 11.0.0.1 is the server –  Adam Schiavone Aug 30 '12 at 0:42

1 Answer 1

This sounds like a DNS issue at the server side, I have experienced this in the past. Ensure that your windows server DNS are manually set, and not hunting the DHCP for them.

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