Shift work results in a misalignment between circadian timing and the sleep/wake schedule, leading to irregular and poor quality sleep. Inconsistent input from the daily light cycle further interferes with circadian entrainment. It has been hypothesized that scheduling the sleep/dark cycle on the night shift could aid in promoting adaptation to night shift work by facilitating appropriate phase shifts. In a simulated shift-work study, we compared the ability of two sleep/dark schedules to shift circadian phase. Our results indicate that scheduled sleep/darkness can aid in adaptation to night shift work by inducing both advance and delay phase shifts, depending on the timing of the sleep schedule, although the size of the phase shifts are not sufficient to produce complete adaptation to the night shift. These results have applications to night shift workers, particularly in occupations in which alterations in the timing of light exposure cannot be achieved during working hours.