The earliest experiences with alcohol for many children occur in the family context with parental supervision. The current study examined individual and sociocultural characteristics associated with early (prior to age 13years) sipping and tasting alcohol with parental permission in two longitudinal community samples. Early sipping/tasting was also tested as a predictor of frequency and quantity of alcohol use, and alcohol-related problems seven years later in late adolescence. Early sipping/tasting with parental permission was associated with a sociocultural context supportive of alcohol use (e.g., parental alcohol use, permissive rules about alcohol use in the home, parental attitudes about underage drinking, perceived peer norms), adolescent sensation seeking and disinhibition (e.g., surgency, externalizing behavior) and appraisals of alcohol (negative outcome expectancies and negative implicit alcohol associations). Early sipping/tasting predicted increased frequency and quantity of alcohol consumption, and increased alcohol-related problems in late adolescence, even after controlling sociocultural and individual difference variables. Findings suggest that early sipping/tasting with parental permission is not benign and is a viable target for preventive interventions.