School connectedness has a significant impact on adolescent outcomes, including reducing risk-taking behavior. This paper critically examines the literature on school-based programs targeting increased connectedness for reductions in risk taking. Fourteen articles describing seven different school-based programs were reviewed. Programs drew on a range of theories to increase school connectedness, and evaluations conducted for the majority of programs demonstrated positive changes in school connectedness, risk behavior, or a combination of the two. Many of the reviewed programs involved widespread school system change, however, which is frequently a complex and time-consuming task. Future research is needed to examine the extent of intervention complexity required to result in change. This review also showed a lack of consistency in the definitions and measurement of connectedness as well as few mediation analyses testing assumptions of impact on risk-taking behavior through increases in school connectedness. Additionally, this review revealed very limited evaluation of the elements of multicomponent programs that are most effective in increasing school connectedness and reducing adolescent risk taking.