For many years, educators and policymakers looking for strategies to close the achievement gap and improve student learning have sought solutions involving new uses of technology, especially for students placed at-risk. Unfortunately, the results of technology initiatives have been mixed. Often, the introduction of technology into classrooms has failed to meet the grand expectations proponents anticipated. The educational landscape is replete with stories and studies about how at-risk students were unable to benefit from particular innovations seeking to use computers for teaching. There are, however, successes among these efforts, and they reveal some common approaches to technology use. Based on a review of more than 70 recent studies, this brief describes these approaches, particularly as they apply to high school students who have been at risk of failing courses and exit examinations or dropping out because of a range of personal factors (such as pregnancy, necessary employment, mobility, and homelessness) and academic factors (special education needs, credit deficiencies, and lack of supports for learning English). The brief then outlines policy strategies that could expand the uses of technology for at-risk high school youth.