In this video-mediated dialogue, seven students in rural Massachusetts discuss factors that led them to drop out of high school. A video of their intimate conversation is then shown to teachers, counselors, and administrators, whose reactions and responses are filmed and shown back to the students. This unique process allows participants on each level of the educational ladder to contribute to a personal and structural understanding of the many factors that derail students from graduating, such as getting held back, confrontation at school, trauma from bullying, and problems at home. The participants generate a number of solutions-based strategies, as each person has the space to be heard, to listen, and to respond. This Video Bridge and Screening Guide provide a springboard for further dialogue and problem solving in classrooms, schools, and districts across the country-particularly in rural areas-about how to help students succeed in finishing high school.