Free online services have become an indelible part of today's Internet usage experience. The online experience of many users centers around web search (Google, Bing), web-based email (Gmail, Hotmail), online social networks (Facebook, MySpace), and video sharing (YouTube). Unfortunately, users are often unaware that they are making their private information available to a company they have no compelling reason to trust. We argue that problems of user privacy have the potential to be addressed with technical solutions over legislative ones. We support this argument with two case studies from our research in privacy and networking.