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So here is my scenario.

I have setup an Ubuntu 14.04 PPTP server setup at a remote site and it is working just fine. I can connect clients remotely via Linux & Windows. I can also ssh and RDP to internal clients on that remote network just fine.

My issue, is related to the fact that my Ubuntu 14.04 client machine (laptop) can connect to the VPN but cannot resolve DNS names via a terminal or a browser. If I start up my Windows virtual (via VirtualBox) and connect to my VPN, I can resolve DNS names just fine through the virtual. My only guess is that for some reason Windows is automatically setting up the right routes and DNS resolution. As far as the technical details to the routes I am not sure how to get that information on either OS.

In my pptp-options file on the remote PPTP server. I have the following for proper DNS routing which points to an internal server on the remote network. Below are those settings.


I don't think that the issue is related to my internal DNS server since all clients on the remote network resolve DNS names just fine for both internal and external names. Also, my Windows virtual is resolving the internal and external machines just fine when connecting. So I think it is related to my Ubuntu 14.04 client (laptop). Is there something else I need to configure on the Ubuntu VPN connection for allowing proper name resolution?

Also, when I connect to the VPN with Ubuntu and use nslookup to resolve machines on the remote network I actually resolve the IP correctly. However, when I try to navigate to the machines with their DNS name via a browser or ssh. It cannot resolve the name at all.

myuser@mymachine:~$ ssh myuser@mymachine.mmb.local
ssh: Could not resolve hostname mymachine: Name or service not known
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The file responsible for system-wide DNS resolvers is /etc/resolv.conf. When you connect to server this file should be updated on client with the information ms-dns set on PPTP server, the VPN client is responsible to make this change, although you can configure it to not make any change on DNS configuration. Also check if you can resolve with nslookup hostname dns-server

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