During adolescence, biological, psychosocial, and contextual factors converge in a “perfect storm” and have been put forward to explain the delay in chronotype observed at this age and the prevalence of disrupted sleep. This study provides evidence to support that chronotype and sleep patterns (particularly sleep duration) are socially constrained and to identify novel significant social predictors. Uruguayan public school activities are arranged in up to 4 shifts, creating a natural experiment to examine the effect of school timing on questionnaire-based assessments of sleep and chronotype. In this study, 268 high school students (15-18 years old) who attended school either on morning (0730 to 1130 h) or afternoon shifts (1130 h to 1530 h) responded to an adapted School Sleep Habits Survey. Students attending afternoon shifts had later chronotypes (a 1.5-h later midpoint of sleep on free days adjusted for sleep debt) than those attending the morning shift. Besides shift, evening social activities (including dinner time) were further identified as key predictors of late chronotypes, whereas age and gender were not. Sleep on school days was overall advanced and reduced with respect to weekends, and these effects were stronger in morning-shift students. Weekend sleep duration was similar between shifts, which probably caused the prevalence of reduced sleep durations (average weekly sleep duration, SDweek <8 h) to be higher in morning-shift students (almost 80%) than in afternoon-shift ones (34%). Reduced sleep duration was significantly higher in morning-shift students. In addition, age, chronotype, and dinner time became relevant determinants of sleep deficit only in the morning-shift students. Besides the important social constraint of early school start time, this is the first study to confirm the significance of other types of social pressures on both adolescents’ chronotype and sleep deficit, which can be useful as potential new targets for effective policies to protect adolescent sleep.