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Sleep deprivation in teenage students is pervasive and a public health concern, but evidence is accumulating that delaying school start times may be an effective countermeasure. Most studies so far assessed static changes in schools start time, using cross-sectional comparisons and one-off sleep measures. When a high school in Germany introduced flexible start times for their senior students—allowing them to choose daily between an 8 am or 9 am start (≥08:50)—we monitored students’ sleep longitudinally using subjective and objective measures. Students (10–12th grade, 14–19 y) were followed 3 weeks prior and 6 weeks into the flexible system via daily sleep diaries (n = 65) and a subcohort via continuous wrist-actimetry (n = 37). Satisfaction and perceived cognitive outcomes were surveyed at study end. Comparisons between 8 am and ≥9 am-starts within the flexible system demonstrated that students slept 1.1 h longer when starting school later—independent of gender, grade, chronotype, and frequency of later starts; sleep offsets were delayed but, importantly, onsets remained unchanged. Sleep quality was increased and alarm-driven waking reduced. However, overall sleep duration in the flexible system was not extended compared to baseline—likely because students did not start later frequently enough. Nonetheless, students were highly satisfied with the flexible system and reported cognitive and sleep improvements. Therefore, flexible systems may present a viable alternative for implementing later school starts to improve teenage sleep if students can be encouraged to use the late-option frequently enough. Flexibility may increase acceptance of school start changes and speculatively even prevent delays in sleep onsets through occasional early starts.