content: when every request outbound from your encrypted server can be catalogued, observed, and isolated back to you?  s/ when / if /  Literally defeats the purpose of a VPN.  The purpose of a VPN is to not send any unencrypted traffic through an entity that's definitely in bed with the US government (including both the ISP and "Big Easy Trustworthy VPN Inc"). It doesn't solve the problem of what's seen downstream (ex. the Web-sites you visit) - no one thing can solve this problem.  Like with Tor.  It's just the first link in the chain.