Drawing on interview and informal observation data collected from eight adolescent African-American boys residing in an urban community and attending an urban charter school, this paper describes and explores their relationships with African-American male school personnel. This paper highlights how adolescent African-American boys' experience and make sense of their interactions with teachers, school administrators and staff, as well as discusses the implications for school engagement and masculine identity development. The boys' narratives reveal relationships that are confrontational and strained, as well as respectful and caring. Furthermore, they highlight the ways in which masculinity is being shaped through the reciprocal-posturing of adult males. (Contains 6 notes and 2 tables.)