This study had two primary objectives: (1) characterize the content of presleep cognitions of chronic pain patients and (2) evaluate the association between presleep cognitions and sleep disturbance. Thirty-one outpatients with benign chronic pain completed the Beck Depression Inventory, pain and sleep diaries and participated in an in vivo, presleep thought sampling procedure for 1 week in their homes. The three most frequently reported presleep cognitions were general pain-related thoughts (36%), thoughts about the experimental procedure (27%), and negative sleep-related thoughts (26%). Stepwise multiple regression analyses found the presleep thoughts pertaining to pain and environmental stimuli were significantly associated with sleep continuity, independent from the effects of depression and nightly pain severity. Pain severity was found to be positively associated with Wake After Sleep Onset Time. These results are consistent with cognitive-behavioral models of primary insomnia and suggest the content of presleep cognitive arousal may contribute to sleep disturbance secondary to pain.