The transition from adolescence to adulthood is filled with new responsibilities, rights, and roles. As such, it can be a difficult period for the individual to navigate, and is only complicated by the presence of complex psychiatric illness. When these factors coincide, what can result is social and psychiatric disability. This article examines unique obstacles and considerations in the care of the complex young adult patient as illustrated by case vignettes from a specialty unit devoted to the care of this population. In the process, specific strategies useful in engaging, assessing, and treating this cohort are put forth.