This study attempted to understand how caregivers’ stress and psychopathology influenced self-reports of their child’s well-being. Participants were recruited from the Children, Intimate Relationships, Conflictual Life Events, and Stress (CIRCLES) study. Male caregivers' reports were more influenced by their psychopathology when compared to female caregivers' reports. In conclusion, male caregivers’ reports are unreliable due to fluctuating stress levels, while female caregivers’ reports are more reliable, even though their psychopathology causes changes in their child’s health.