I have Mac OS X Host, Ubuntu Guest/VM, Shared Networking. When I'm connected to the "internet", everything works fine. I can ping my Ubuntu VM (named 'ubuntu') just fine using ping ubuntu.local However, I often have to connect my Mac to a company VPN (Juniper), which then causes the Mac's IP address to change to a different subnet. Once that happens, the Mac can no longer ping/hit the VM. In my case, after VPN connection, the Mac IP==10.1.115.78, and the Ubuntu IP==10.211.55.4. Note that the name resolution still works; ping ubuntu.local still resolves to 10.211.55.4, it's just that the Mac no longer has a 'route' to that IP. I am assuming there is a really easy fix for this (as you can tell I am a networking idiot). I've tried switching the Parallels networking type to Bridged, Host only, etc, to no avail. Ideally I want the routes to work whether the Mac is connected to VPN or not, and I want the Ubuntu to continue to have internet access. Do I have to add a hard-route to the Mac's route tables or something?