I have an ubuntu VM running on Hyper-V which connects to a VPN service. When the VM is connected to the VPN I am unable to ping / connect to the host machine. Samba mounts won't get mapped, ping packets time out. What can I check in order to fix this?
It will be a setting enforced by your VPN provider. For example Cisco AnyClient VPN has such a setting that can effectively disconnect it from the LAN and force all traffic through the VPN.
I think it does it by removing all routes to the local LAN - you may be able to re-add the route and regain access to the LAN.
Unfortunately you don't say what VPN client you use and what VPN service. Is it some public one or a corporate VPN?