Adolescents become the subjects of experimentation in the mental health profession, as we try to figure out new and effective ways to treat and understand the next generation of young adults coming of age. Even when attempting to use the most up-to-date, ‘evidence-based’ practice, by the time the evidence is gathered, adolescents living in a technological age have developed new ways of communicating and relating to their peers, and new ideas about themselves, always staying one step ahead of the research. Considering the constant evolution of technology and the ever-changing nature of adolescent development, parents and practitioners alike are left questioning how to manage our technological world and our relationships with our teenage clients. As such, this chapter seeks to explore one particular area of social work clinical practice: the relationship between the technology utilized by adolescents and traditional conceptions of trauma. This chapter concludes that approaches to treating adolescents in the technological era must include joining these “digital natives” in the reality of their digital experiences, an openness to allowing the client define what is and is not traumatic, and to allow for empowered and informed adolescent exploration and identity development in the digital world.