This study used the Take Action goal attainment lesson package and assistive technology to teach nine high school students with mild to moderate disabilities to attain annual transition goals. The Take Action lessons increased students’ goal attainment knowledge, and this knowledge generalized to improved Plan Organizers, and slightly increased students attaining transition goals. Added weekly teacher check-ins improved adjusting plan components that did not work and goal attainment increased. Students who took action on four or five Plan Organizer components attained the most goals, and on average, students used four weekly Plan Organizers to attain a goal. Stronger interventions need to be developed to enable more students to increase the action taken on Plan Organizer components.