An integral change that occurs during adolescence is the development of independent close relationships outside of the immediate family unit. In addition to relationships with peers, adolescents are commonly engaged in natural mentoring relationships. Natural mentoring relationships are organically formed mentoring bonds between youth and adults in their pre-existing social networks. In an effort to better uncover factors that contribute to the development of natural mentoring relationships among Black adolescents, the current study examined a pathway between adolescents’ attachment to their parents and the quantity of natural mentors they possessed via their perceptions of adults as helpful. Survey data from 217 Black adolescents and interview data from a subsample of participants ( n = 25) and their parents ( n = 25) were utilized. Our findings document how parent-adolescent attachment is experienced among Black families and how attachment may shape adolescents’ willingness to pursue supportive relationships with non-parental adults. In addition, our findings indicate that more secure parent-adolescent attachment predict greater quantity of natural mentoring relationships indirectly via greater perceptions of adults as helpful. Implications of study findings for the promotion of natural mentoring relationships among Black youth are discussed.