Sleep can be seen as a biologically driven behavior shaped by cultural context. A "poor fit" occurs when contextual demands for the timing and duration sleep periods are incompatible with the underlying biology. Such contextual factors are well-known for adults, yet little is known of the contextual factors that shape young children's sleep health and to what degree such factors impact sleep duration, timing, and quality. This study attempted to identify how the transition to kindergarten was associated with changes in sleep timing, duration, and quality for children enrolled in preschool prior to attending kindergarten vs. those who were not. Wrist actigraphy in 38 5-year-old children was collected at three longitudinal points before and after the start of kindergarten. Our data suggested that the transition to kindergarten was associated with a reduction in weekday sleep (mostly due to lost napping) and an advance in the weekday nocturnal sleep period that was most pronounced for children not enrolled in preschool prior to kindergarten. These sleep changes paralleled objective and caregiver-reported data of increased sleep pressure that lasted well into the first month of kindergarten.