Despite our best efforts, pediatric obesity remains an important public health issue. Although many different approaches to address this condition have been utilized, few have achieved long-term success. Technology is increasingly being explored as a convenient and accessible method for delivering behavioral interventions. Stephens and colleagues report the feasibility of using a behavioral coaching social chatbot, Tess, to extend a multicomponent pediatric obesity intervention for adolescents. We examine the pros and cons of this approach. Although social chatbots offer an interesting and novel method for promoting round-the-clock support, important issues and decisions must be carefully considered during the design phase to help ensure a safe environment for a vulnerable population.