Re: Obession with (free) Wi-Fi
Yes, insecurely, unfortunately. Same as if the VPN happens to disconnect temporarily, or you lose coverage, etc etc.
The OpenVPN client has a setting to stop all traffic at such times. I do not know if it is reliable as I haven't got round to actually testing it (I know with that setting turned off that OpenVPN uses whatever route the data wants to take when there is no connection). I'd hope other VPN apps (esp any paid-for ones) can be set to do the same.