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Research characterizing the adolescent drinking context is limited, often relies on samples of current drinkers reporting on recent/last or typical drinking experiences, and provides little information about the context of very early use. The present study uses repeated monthly assessments to describe the context of drinking days and matched nondrinking days to determine the unique risk associated with different drinking-related characteristics. Additionally, we used latent class analysis to empirically identify key configurations of drinking-related characteristics and both family- and nonfamily-related environmental characteristics (social context, physical location, source of alcohol). Data included 688 days (344 drinking days, 344 nondrinking days) from 164 middle-school students enrolled in a prospective study on drinking initiation and progression (62% female; 26% non-White, 11% Hispanic). Results supported 4 patterns: (a) heavier drinking occurring in a peer context, lighter drinking occurring in (b) a family context or (c) a peer context, and (d) drinking alcohol obtained at home without permission. Latent classes varied as a function of gender, age, peer norms, and parenting behaviors as well as alcohol type and perceived alcohol availability. Findings indicated that highly endorsed contexts were not necessarily the riskiest ones, and simply targeting an oft-reported source of alcohol, physical location, or social context may not be an effective strategy for reducing underage drinking. Additionally, although greater monitoring and anticipated parent reaction to drinking are typically protective against adolescent drinking, we found they were associated with parent-sanctioned drinking, suggesting the role of parenting practices must be considered in the context of drinking pattern.