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Abstract Objectives Sleep and pain are co-occurring issues in adulthood. Pain reactivity to worse sleep refers to person-specific changes in daily pain following nights of shorter-than-usual sleep duration or poorer-than-usual sleep quality. We examined the cross-sectional and longitudinal associations of sleep-related pain reactivity with psychological distress and the number of chronic conditions. Methods Data were obtained from the Work, Family, and Health Study, which collected data from healthcare and information technology workers (n = 311; Mage=41.38 years), who completed 8-days of daily diary. We controlled for sociodemographic and health covariates in a series of multilevel structural equation models and growth curve models in Mplus. Sensitivity analyses adjusted for sleep and pain medications and stratified analyses by age. Results Those who reported more pain locations and severity following poorer-than-usual sleep quality had more concurrent distress (higher pain location reactivity to worse sleep quality: B = 1.03, p<.001; higher pain severity reactivity to worse sleep quality: B = 0.56, p=.001). In the growth curve models, higher pain location reactivity to poorer sleep quality was associated with higher concurrent distress (Path Est.=1.67, p=.023) and decreases in distress over time (Path Est.=-0.74, p=.032). Higher pain severity reactivity to poorer sleep quality was associated with higher concurrent distress (Path Est.=0.62, p=.030) but not changes in distress over time. Pain reactivity to worse sleep was not associated with concurrent or change in the number of chronic conditions. Discussion Future directions are to examine the influence of pain reactivity to worse sleep in larger and more diverse samples across longer follow-up periods.