We investigated children and families who were participating in a mentoring program targeting children with incarcerated parents. Using multiple methods and informants, we explored the development of the mentoring relationship, challenges and benefits of mentoring children with incarcerated parents, and match termination in 57 mentor-child dyads. More than one-third of matches terminated during the first 6 months of participation. For those matches that continued to meet, however, children who saw their mentors more frequently exhibited fewer internalizing and externalizing symptoms. In monthly interviews with participants, themes emerged about challenges associated with mentoring and reasons for match termination. Implications for researchers, practitioners, and policymakers are discussed.