For this audience, one would assume this isn't anything new. The next level of 'detail'/risk to consider here is the fact that so many apps, and even browsers,

For this audience, one would assume this isn't anything new. The next level of 'detail'/risk to consider here is the fact that so many apps, and even browsers, will bind to the "on connection" event of connecting to a wifi hotspot - before you can initiate your VPN your twitter client* has already sent your authenticated token over the wire, etc. I've tried to hack something together with iptables but that doesn't work either in airports/etc where there are splash screens to negotiate, etc. ( = yes, you could use a better client, but then the reason we need VPNs in the first place is that so many apps and sites don't use https)