For children residing in institutional settings, staff act as primary caregivers and often provide assessment of child psychopathology. Minimal research exists on how and when staff-caregivers are best positioned to report on youth mental health. This study examines differences between 60 staff-reported and 60 adolescent-reported Child Behavioral Checklist/Youth Self-Report (CBCL/YSR) scores in Jordanian care centers, and the associations between adolescent-staff agreement, demographic characteristics and child-caregiver relationship factors. Results indicated small to modest correlations between informant scores. Additionally, staff-caregivers who know the child over 1 year and have a high perceived fit are better able to approximate the adolescent's self-report of psychopathology.