This prospective quasi-experiment (N = 175; mean age = 15.14 years) investigates changes in adolescents' sleep from low-stress (regular school week) to high-stress times (exam week), and examines the (moderating) role of chronic sleep reduction, baseline stress, and gender. Sleep was monitored over three consecutive weeks using actigraphy. Adolescents' sleep was more fragmented during the high-stress time than during the low-stress time, meaning that individuals slept more restless during stressful times. However, sleep efficiency, total sleep time, and sleep onset latency remained stable throughout the three consecutive weeks. High chronic sleep reduction was related to later bedtimes, later sleep start times, later sleep end times, later getting up times, and more time spent in bed. Furthermore, low chronic sleep reduction and high baseline stress levels were related to more fragmented sleep during stressful times. This study shows that stressful times can have negative effects on adolescents' sleep fragmentation, especially for adolescents with low chronic sleep reduction or high baseline stress levels.