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Two VPNs, one accesses DNS properly, one does not.

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I have two Offices with two separate RRAS servers setup in each one on Windows 2012

Office 1

  • DHCP server on separate VM from RRAS server.
  • RRAS Server on VM

Office 2

  • RRAS and DHCP servers on same VM

Both DHCP servers and RRAS servers are configured exactly the same except, of course, the DHCP server scopes are different subnets. I literally brought both up in two different screens and went screen by screen.

I running a Mac at home, however, I have the same problem on my PC. If I connect to the VPN in Office 1. Then run nslookup and do a DNS lookup, it uses my VPN's DNS servers and resolves the IP.  If I connect to the VPN in Office 2. Then run NSLookup and do a DNS Lookup, it shows me that I'm using my local (to my Mac) DNS servers and it won't resolve the IP.

I have checked my Mac (and PC) VPN settings and they are also identical.

I don't even know where to check to solve this problem.


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