Study Objectives: The goal of this study was to examine daily associations between sleep and cognition in older adults suffering from insomnia, with or without a history of chronic pain. Methods: Sixty older adults with insomnia and a history of chronic pain (HxCP; n = 33, mean age = 69.5 years, standard deviation = 7.8) or no history of chronic pain (NCP; n = 27, mean age = 69.7 years, standard deviation = 7.9) completed 14 days of diaries and actigraphy, measuring sleep onset latency (SOL), wake after sleep onset (WASO), sleep efficiency (SE), and sleep quality. Participants completed daily cognitive measures of processing speed (ie, symbol digit modalities test, SDMT), reasoning (ie, letter series), and verbal memory (ie, word list delayed recall). For HxCP and NCP, associations between sleep parameters, daily pain, depressive symptoms (ie, Beck Depression Inventory, Second Edition scores), and daily cognition, controlling for age, and global cognition were examined through multilevel modeling. Results: For HxCP, greater self-reported WASO was associated with worse next-day SDMT performance, whereas greater actigraphic WASO was associated with better next-day SDMT performance. Greater depression was associated with worse daily letter series performance. Greater self-reported WASO and SE were associated with better next-day delayed recall. For NCP, greater self-reported WASO and depression were associated with better daily SDMT performance, whereas worse daily pain was associated with worse SDMT and delayed recall performance. Conclusions: In older adults with HxCP, improving sleep may benefit lower level cognition, whereas reducing depression may affect higher level cognition. Discrepancies in sleep parameters promote assessment of objective and subjective sleep outcomes when investigating effects of insomnia on cognition.