Abstract Study Objectives To investigate the short- and longer-term impact of a 45-min delay in school start time on sleep and well-being of adolescents. Methods The sample consisted of 375 students in grades 7–10 (mean age ± SD: 14.6 ± 1.15 years) from an all-girls’ secondary school in Singapore that delayed its start time from 07:30 to 08:15. Self-reports of sleep timing, sleepiness, and well-being (depressive symptoms and mood) were obtained at baseline prior to the delay, and at approximately 1 and 9 months after the delay. Total sleep time (TST) was evaluated via actigraphy. Results After 1 month, bedtimes on school nights were delayed by 9.0 min, while rise times were delayed by 31.6 min, resulting in an increase in time in bed (TIB) of 23.2 min. After 9 months, the increase in TIB was sustained, and TST increased by 10.0 min relative to baseline. Participants also reported lower levels of subjective sleepiness and improvement in well-being at both follow-ups. Notably, greater increase in sleep duration on school nights was associated with greater improvement in alertness and well-being. Conclusions Delaying school start time can result in sustained benefits on sleep duration, daytime alertness, and mental well-being even within a culture where trading sleep for academic success is widespread.