Using archival data from the Family Pathways Project, an exploration of how mothers experienced parenting their adolescents in the context of a role-reversed attachment was conducted. Four mothers who had experiences parenting an adolescent who had been previously classified as role-reversed were selected. In each of the four Experiences of Caregiving interviews, the mothers explored their experiences of parenting and revealed their personal perspectives on the relationship between mother and child. Case-specific themes related to each mother's view on the relational experiences, affective and cognitive components of parenting, as well as experiences during separation and transition were reported. These themes were parental reliance on adolescent support, parental experiences of powerlessness, parental needs for emotional support, resilience in the context of role-reversal and awareness of developmental transitions. Given the applicability of the findings, clinical implications related to role-reversed attachment from adolescent to mother suggested how the repercussions for the dyad can be mediated through therapeutic understanding and support.