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Despite annual fluctuations in the exact percentages of adolescents in the United States who are involved with problem behaviors such as alcohol consumption, unprotected sexual intercourse, and illicit drug use over the past decade, a large proportion of youth have been introduced to, and continue to engage in these behaviors. In response, researchers and clinicians have continued their search for variables that are correlated with adolescent risk involvement including variables within the family context. Previous research has linked parental monitoring (i.e., knowledge of an adolescent's whereabouts and activities) and parents' appropriate modeling of behaviors to reduced adolescent risk involvement. Problem behavior also has been associated with impaired parent-adolescent communication and family dynamics including familial conflict and perceived lack of support. While much of this research has shown that some aspects of the family environment, as well as parental behaviors (e.g., parental monitoring and modeling of inappropriate behaviors), vary across relationships and families, little is known about where and why this variability exists. A model that hypothesized direct relationships between caregiver appraisals of the family environment, caregiver coping strategy use, and caregiver behaviors, and adolescent problem behavior was proposed in the present study. Path analyses findings revealed that this model adequately fit the data and therefore was a good representation of processes leading to the behaviors previously linked to adolescent problem behavior (i.e., monitoring and modeling behaviors). Exploratory analyses were conducted in which the model was modified by deleting the family appraisal variables. Eliminating the family appraisal variables increased the fit of the proposed model. Reasons for eliminating these variables and implications of the modified model are discussed. Additional exploratory analyses were conducted testing the significance of the model using individual adolescent problem behaviors (e.g., violence, drug use) as outcome measures. All of these models were adequate representations of the data. Specific paths among model variables are discussed in more detail. These models are, therefore, efficacious as theoretical foundations for educational and intervention purposes to target caregiver cognitions and behaviors related to adolescent problem behavior.