As you can see, two servers are connected and they answer correctly on the command line and in applications. The ppp0 connection is the VPN connection. Reach : Reachable,Directly Reachable Address There is a notable difference in the lookup order: connecting using WLAN: Using scutil -dns I dumped the DNS configuration when connecting via WLAN vs. Command line tools like host name will correctly resolve the IP address, ping name will not resolve. However, when I use a dial-up connection (Huawei HSDPA USB Stick) host names are not correctly resolved in applications (e.g. Everything works great when establishing the VPN connection via LAN or WLAN. I am using a MacBook with Mac OS X 10.8.2 and connect to my company's network via VPN.