Adolescent alienation is particularly relevant in the school environment. The phenomenon of alienation describes a student’s level of academic and social disengagement from school. There is considerable evidence that a student’s experience of alienation is profoundly shaped by psychological and personal factors, yet school factors including inequitable expectations, grading, and discipline policies also contribute to a student’s feeling of disconnection. This paper presents the findings of a phenomenological study which examined the experiences of males aged 16 to 19 who self-identified as being alienated from their school system. Five participants engaged in three semi-structured interviews and one perception check. Descriptions revealed common themes throughout the structure of the experience. These themes were: (1) need to build relationships despite negative consequences, (2) loss of trust in school adults, and (3) fear of failure and of disappointing self and family. The invariant structure (essence) that emerged was the interrelationship among these themes as related to belonging, trust, and self-worth. The paper further explores the idea that developmental, comprehensive school counseling programs that target inequitable school practices and policies will reduce the number of adolescents feeling a sense of alienation from school, from educators, and from learning.