During the past decade, there has been an increasing gender achievement gap with male students lagging behind their female counterparts on a number of important indicators of school success. This article examines recommendations and strategies for school counselors working with middle school boys to enhance the learning environment, to promote strengths, and to encourage positive attitudes toward academic achievement and future planning. Collaboration with teachers, administrators, parents, and community members as important stakeholders can offer combined resources to promote school success. The strategies described have resulted from a local collaborative action research project conducted by counselor educators and students, the county supervisor of guidance, and middle school counselors.