The transition from high school to college is marked by many changes, one of the most significant being the increased accessibility of alcohol, putting college students at high risk for alcohol-related consequences. It is imperative to identify factors that can protect young adults against these risks during this critical period. Although peers become increasingly influential in college, extant literature has shown that parents still have an impact on their children's behavior during this time. While parents spend less time with their children after college matriculation, they may indirectly protect against risky drinking behaviors by instilling certain values into their children before they make this transition. Using data from a large sample of students during their senior year of high school and their freshman year of college, the current study sought to examine interactive effects of parental communication and parental knowledge and caring on drinking behavior, and the extent to which internalization of personal drinking values mediate these effects. The primary study hypotheses were tested using path analysis conducted in Mplus 7.0. Full information maximum likelihood (FIML) estimation was utilized to estimate missing data and bootstrapping was used to address non-normality in the data. Results showed that, for those whose parents were high in knowledge and caring, higher levels of communication were associated with lower risk for alcohol use and problems at wave 3 through less permissive drinking values at wave 1. This finding has important implications for prevention approaches designed to reduce risk for heavy drinking and related problems during the transition to college.