Alternative education is one of the contexts that receives little attention in research and practice. This narrative inquiry study explores the narrative of a school counselor at a continuation high school to better understand his experiences, challenges, contradictions, and opportunities of serving in an unfamiliar educational sector. This paper provides recommendations for policy and practice, specifically for professional school counselors, school district counseling personnel, and counselor educators to consider in their efforts to support counselors and students in continuation high schools/alternative education.