Children with psychologically vulnerable caregivers may be at risk for being labeled as having behavior problems when typical behaviors are viewed by their caregivers as problematic. Research examining the accuracy of the caregivers’ perceptions of children’s behaviors is limited. The purpose of this study was to use the Resiliency Model of Family Stress, Adjustment, and Adaptation to explore family and female caregiver factors associated with appraisals of children’s behaviors, the extent to which these appraisals may be distorted and children’s level of risk of having behavioral problems. A cross-sectional, correlational design was used. Data were collected from female caregivers of preschoolers. Reliable and valid instruments measured family factors, demographic characteristics, comfort in parenting, appraisal of behaviors, daily stress, parenting stress, depressive symptoms, social support, ratings of children’s behaviors, and distortion in the ratings. Analyses included ANOVA, ANCOVA, Chi-square, simultaneous and hierarchical linear regressions. Results indicated that family typology was not associated with the female caregivers’ appraisals of children’s behaviors or distortion of caregivers’ ratings of behaviors; however, it was associated with risk of having children with behavioral problems. In the simultaneous regressions models, greater discomfort with parenting and greater perceived daily stress were associated with more negative appraisals of children’s behaviors by the female caregivers and Caucasian race and higher distortion in behavioral ratings were associated with higher risk of behavioral problems in children. Social support did not buffer the effects of caregiver depression on appraisals of children’s behaviors or level of risk of children having behavioral problems.