Black, school-aged youth may experience socioeconomic, psychological, and emotional difficulties that affect their mental health, leading to maladaptive ways of coping, such as cannabis use. Instead of getting treatment and support to help them manage their stressors in positive ways, Black youth often receive punitive school practices, including referrals to the juvenile justice system. Counselors who work with school-aged youth are likely to encounter many Black youth and can thus either be instrumental to their psychological development or inadvertently impede their well-being with over-pathologization and criminalization of their cannabis use. In this article, the author reflects on a particular experience he had working with a Black youth and how it influenced his cultural competency and development as a counselor. The author also discusses the socioeconomic landscape and psychological experience of Black youth and their rationale for cannabis use. The article concludes with implications for professional counselors.