Middle level teachers and administrators working in small or rural schools often face unique obstacles in implementing recommended middle level practices. From sharing staff and schedules with other school sites, to inappropriate instructional techniques, to a general lack of understanding of the middle level philosophy, these obstacles can be a source of frustration for school leaders and hinder school improvement initiatives. A better understanding of these issues and the discussion of potential solutions will benefit teachers, administrators, and policy makers in improving middle level education in rural communities. By building on the positive characteristics found in rural and smaller schools, as well as identifying and addressing the obstacles encountered at smaller schools, middle level leaders can create and maintain distinctive and effective programs for their students.