In her book Failure to Connect: How computers affect our Children’s Minds, sounded the alarm to the educational community that computers would not impact the intellectual growth of children in the ways that had been anticipated by the Clinton Administration when they started the push to have the world-wide web integrated into American classrooms by passing the Classroom 2000 education initiative. In a speech in April of 2013, Clinton would follow-up by saying that the modern internet has forced a change in what we consider to be forms of good citizenship. The future will redefine how we should act and interact. Unfortunately, while there have been definite gains in the ease of accessing information from a variety of sources using the internet, it now appears that the internet might also be having a seriously negative effect on students. It is now becoming evident that the internet has redefined and expanded the meaning of bullying. The emergence of social media sites and its impact within the repertoire of high school and college students needs to be tested empirically as well as in the court of law. Recently, however, a new trend has emerged and is observed in the establishment of anonymous “confession” sites tied into college and high school campuses. These sites appear to be an extension of the impact of Facebook and Twitter on students, and unfortunately, much of what is being witnessed on those sites is negative and hurtful and it is proving to be a challenge for administrators, teachers and parents to understand or control. The ability to remain anonymous and to add hashtags (#) for emphasis is often misused by adolescents who don’t always think through the end result of actions.