A large number of studies have shown a close association between the 24-hour rhythms in core body temperature and sleep propensity. More recently, studies have have begun to elucidate an intriguing association of sleep with skin temperature as well. The present chapter addresses the association of sleep and alertness with skin temperature. It discusses whether the association could reflect common underlying drivers of both sleep propensity and skin vasodilation; whether it could reflect efferents of sleep-regulating brain circuits to thermoregulatory circuits; and whether skin temperature could provide afferent input to sleep-regulating brain circuits. Sleep regulation and concomitant changes in skin temperature are systematically discussed and three parallel factors suggested: a circadian clock mechanism, a homeostatic hourglass mechanism, and a third set of sleep-permissive and wake-promoting factors that gate the effectiveness of signals from the clock and hourglass in the actual induction of sleep or maintenance of alert wakefulness. The chapter moreover discusses how the association between skin temperature and arousal can change with sleep deprivation and insomnia. Finally it addresses whether the promising laboratory findings on the effects of skin temperature manipulations on vigilance can be applied to improve sleep in everyday life.