Napping can enhance alertness during sustained wakefulness, but the importance of the temporal placement of the nap between days and within the circadian cycle remains controversial. To resolve these issues, a between-groups study was conducted with 41 healthy, young adults permitted a 2-h nap at one of five times during a 56-h period otherwise devoid of sleep. Naps were placed 12 h apart, near the circadian peak (P) or trough (T), and were preceded by 6, 18, 30, 42, or 54 h of wakefulness. Visual reaction time (RT) performance, Stanford Sleepiness Scale (SSS) ratings, and sublingual temperature were assessed every few hours throughout the 56 h, which took place in an environment free of time cues. All groups displayed a circadian-modulated decline in RT measures and increases in SSS functions as sleep loss progressed. A nap placed at any time in the protocol improved RT performance, particularly in the lapse domain, but not SSS ratings. Comparisons within groups of circadian temperature cycles for the first versus second day of the protocol indicated that early naps (P6, T18, P30) tended to prevent the mean drop in temperature across days. The earlier naps (P6, T18) yielded more robust and longer lasting RT performance benefits, which extended beyond 24 h after the naps, despite the fact that they were comprised of lighter sleep than later naps. Circadian placement of naps (P vs. T) did not affect the results on any parameter. In terms of temporal placement, therefore, napping prior to a night of sleep loss is more important for meeting subsequent performance demands than is the circadian placement of the nap. SSS ratings suggest that the napper is not aware of these performance benefits. Because the longest lasting RT gains followed early naps, which were composed of less deep sleep than later naps, napping during prolonged sleep loss may serve to prevent sleepiness more readily than it permits recovery from it.