Although there are many transitions that occur in a young person’s life, transition from high school to adulthood can be one of the most challenging. This transition requires autonomy and decision-making skills. To support youth in having positive outcomes after high school, it is imperative for teachers to have strategies to guide students in making informed decisions as they begin the transition process. This article provides teachers with strategies and resources to help youth build autonomy, make informed decisions, and gain information via web-based resources to support the transition from high school into postschool life. Steps for building autonomy, evaluating web-based resources, and investigating web-based resources to support transition are included.