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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.


Lets say the the VPN server also hosts a website

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

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

HOWEVER: I tried running the command dig @myServersIpHere 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?


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

Non-authoritative answer:  canonical name =
share|improve this question
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. is the server – Adam Schiavone Aug 30 '12 at 0:42

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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