As the United States public school classrooms encounter notable shifts in student demographics and increased access to technology, teachers face the dual challenges of cultural and digital differences as they attempt to build relationships with students and develop responsive and relevant instruction. Framed by culturally responsive teaching (CRT), this qualitative study explored how one middle school teacher and his students in two summer school English classes interacted with and responded to novel technology-based instructional approach that sought to connect the students' lives outside of school to the classroom. The findings suggest that involving the students within this culturally responsive teaching approach using student-created videos informs the contribution of both the teacher and the students for connecting home and school contexts with a CRT framework.