Cumulative risk theory suggests that a variety of social risk factors would have an additive effect on obesity risk. Multiple studies have suggested that obesity is related to basic resources such as transportation and financial resources. Additional research points to parental engagement and parental monitoring as additional sources of risk. This study investigates the cumulative risk of these variables in an at-risk preschool population. Teachers at 27 Head Start centers were trained in a structured interview process called the Family Map (FM). The FM is used to identify potential risk factors that affect child learning and development, toward the provision of educational services, supportive interventions, and referrals to community services. Results confirm that basic resources are related to Fruit/Vegetable (F/V) consumption. However, this study identified multiple additional variables connected to parental engagement (providing routines, parenting behaviors, discipline), and parental monitoring (activity monitoring and injury prevention behaviors) that were also related to F/V consumption. When a cumulative risk model was applied, parental engagement and parental monitoring were predictive of F/V consumption, but not basic resources. The study's findings identify a host of family and parent variables that are related to F/V consumption within a cumulative risk framework that highlight the importance of parenting above and beyond basic resources. Implications for prevention/intervention program development are discussed.