We describe a sample of school-age children of incarcerated parents enrolled in a federally funded mentoring program. A mixed methods approach was applied to discern key themes related to caregiver incarceration. Results demonstrated a high prevalence of posttraumatic stress as well as high rates of internalizing and externalizing behaviors. Descriptions of children's stress and coping behaviors in response to the ambiguous loss associated with parental incarceration are presented. Further, implications for similar mentoring programs are discussed.