Sleep complaints are common among older adults with chronic pain. Because of the risk of significant side effects, sleep medications are not recommended as first-line treatments. Little is known about the association between positive psychosocial factors and sleep, but further awareness could support non-drug strategies to minimize poor sleep. The purpose of this study was to (1) determine the prevalence of self-reported poor sleep quality and short/long sleep duration in a population of older adults with chronic pain, and (2) examine the associations of negative risk factors, sleep-inducing medications, and positive psychosocial characteristics on sleep outcomes in this population. This study analyzed survey responses from 4201 adults ages ≥65 years with diagnosed back pain, osteoarthritis, and/or rheumatoid arthritis, and at least 1 year of continuous medical and drug plan enrollment. The most commonly reported sleep outcome was short sleep duration (39%), followed by poor sleep quality (22%), and long sleep duration (9%). Based on pharmaceutical claims, prescriptions for opioids (59%) or benzodiazepines (22%) were common. Perceived stress, depression, and pain or sleep prescription medications were independently associated with poor sleep quality and short or long sleep durations. The positive psychosocial factors of higher resilience and more diverse social networks were independently associated with good sleep quality and optimal sleep duration. These results underscore the importance of social and coping factors to sleep, which may provide new opportunities to improve sleep and well-being in older adults with chronic pain.