Objective: We examined associations between sleep problems, distress intolerance, and perceived stress and health in a convenience sample of homeless adults. Methods: Participants (N = 513, 36% women, Mage = 44.5 ±11.9) self-reported sleep adequacy, sleep duration, unintentional sleep during the daytime, distress tolerance, urban stress, and days of poor mental health and days of poor physical health over the last month. The indirect effects of sleep problems on stress and health through distress tolerance were examined using a non-parametric, bias-corrected bootstrapping procedure. Results: Sleep problems were prevalent (eg, 13.0 ±11.4 days of inadequate sleep and 4.7 ±7.9 days of unintentionally falling asleep during the preceding month). Distress intolerance partially accounted for the associations of inadequate sleep and unintentionally falling asleep, but not sleep duration, with urban stress and more days of poor mental and physical health. Conclusions: Many homeless individuals endure sleep problems. Given the connections between sleep and morbidity and mortality, results further support the need for more attention directed toward facilitating improvements in sleep quality to improve the quality of life of homeless adults, potentially including attention to improving distress tolerance skills.