Objective. The purpose of this study was to investigate the nature of sleep problems in veterans presenting to a pain clinic, factors that predict likelihood of being prescribed a sleep medication, types of medications prescribed, and the relationships between sleep medication use and sleep quality, pain, and depression. Design/Setting/Patients. Participants were 201 consecutive patients referred to a Veterans Affairs outpatient pain clinic. They were administered the Pittsburgh Sleep Quality Index, Multidimensional Pain Inventory, and Beck Depression Inventory at intake and 2-month follow-up. Sleep and opioid medication prescriptions were also monitored. Results. Pain severity did not predict global sleep quality; global sleep quality was not predictive of pain severity. Greater depression predicted both more severe pain and more sleep impairment. Having previously been prescribed such medications was the only significant predictor of being prescribed a sleep medication at the time of the 2-month assessment. For the 45% of participants on sleep medications, these medications were not associated with any significant change in pain factors or depression. However, sleep medication use was associated with worse global sleep quality, sleep duration, and sleep efficiency. Opioid prescription was not a significant predictor of sleep factors, pain-related variables, or depression symptoms. Discussion. Results suggest depression may contribute more significantly to sleep problems than pain-related variables in this population. The data suggest the need for controlled, prospective studies of sleep medication to further investigate the impact of sleep medications on sleep components in patients with chronic pain.