ABSTRACT Background & Objectives A growing body of work supports linear associations between sleep and socioemotional adjustment in adolescence. However, associations between sleep and adjustment are not necessarily linear and investigations of nonlinear effects are scarce. This study examined linear and nonlinear relations between several sleep-wake parameters and externalizing behavior and internalizing symptoms in adolescence, and assessed the role of adolescent sex as a moderator of effects. Participants Participants were high school students (N = 180; M age = 17.49, SD = .62; 59% female; 68% White/European American, 32% Black/African American) from a wide range of socio-economic backgrounds living in semirural communities and small towns in Alabama. Methods Sleep-wake parameters were indexed by actigraphy-derived sleep minutes and adolescents’ reports on morningness-eveningness (circadian preference), sleep-wake problems (sleep quality), and sleepiness. Adolescents completed questionnaires on externalizing behaviors and internalizing symptoms. Results Controlling for sleep duration, a higher preference for eveningness and poor sleep quality were associated in a linear fashion with increased externalizing and internalizing symptoms. Nonlinear relations between sleepiness and internalizing symptoms emerged with pronounced sex-related effects, including somewhat delayed accelerating relations for males and rapidly accelerating associations that tended to plateau for females. Conclusions Results illustrate the importance of examining multiple sleep-wake and adjustment variables as well as linear and nonlinear associations.