Background Chronic pain conditions affect up to one third of the adult population in the United Kingdom. Sleep problems are prevalent and negatively impact quality of life. Lack of standardised tools for routine screening and assessment of sleep changes have been a barrier for sleep management. Novel sleep wearables offer an exciting and accessible way to measure sleep but have not been tested outside of the consumer-led landscape and are not commonly used in research and clinical settings. Aims The study aimed to explore the feasibility and acceptability of a sleep monitoring headband (Dreem 2) utilising EEG technology and accompanying smartphone application among a cohort of adults with chronic pain. Results Twenty-one adults (81% women) completed a one-week home sleep study using a sleep headband and accompanying app. Ninety per cent of participants met the pre-defined requirement of two-night's sleep recording. All participants recorded one night of sleep data via the sleep headband. The majority (76%) of participants were satisfied with the sleep study, and 86% of participants were willing to wear the headband longer than the 2-night minimum requirement. Finally, 76% reported the headband as ‘somewhat’ or ‘extremely’ comfortable whist awake; 57% rated the headband as comfortable during sleep. Conclusion The Dreem 2 headband appears to be a feasible and acceptable means of collecting sleep measurements among individuals with chronic pain, despite common sleep disturbances. These devices may have utility for screening, assessment and monitoring in research and practice. Further research is needed to provide guidelines and training for integration.