Mentoring programs intend to provide a supplemental relationship for children who are facing adversity and threats to positive personal development, but they are not intended to replace or interfere with the child's primary attachments to family members. Maintaining and nurturing family relationships through mentoring programs for prisoners' children is a challenge for mentors and mentoring agencies. The children of prisoners are typically in the custody of various types of caregivers while their parents are in prison. Mentors must work with these caregivers to build their trust and cooperation in pursuing strategies that are best for the children. Without the readiness of mentors to understand, respect, and collaborate with caregivers, the longevity of the mentoring match is in jeopardy. Also, children of inmates are often faced with loyalty conflicts between incarcerated parents and caregivers. Loyalty conflicts may also arise in the mentoring relationship if the child starts comparing his/her relationship with the mentor to the relationships with caregivers and incarcerated parents. The child's anxiety about loyalties can be relieved if all the adults in his/her world are continually communicating about what is affecting the child and how best to address it. The mentoring relationship must honor and nourish the significance of the parent-child relationship; and the mentor must recognize and abide by the boundaries and limitations of the mentoring relationship, which means having a clear understanding of his/her supplementary role in the child's life. Suggestions are offered for how the policies and practices of mentoring agencies can facilitate family involvement in the child's development. 9 references