Sleep disorders associated with shift work impair alertness and increase risk of chronic physical and mental health disease. Though studying sleep aids in atrisk populations such as shift workers is critical to improving wellness, implementing robust studies to evaluate wellness interventions in live populations can be particularly challenging.We performed a prospective, single-subject design study in which we assessed the effect of noise-masking earbuds on sleep quality, sleepiness, and stress level in health care shift workers. Despite being gifted the technology at the end of the study, we faced poor participant accrual and study retention. Additionally, robust analysis of our intervention's impact on post-shift alertness was underpowered due to variable participant scheduling. In order to make meaningful advances in improving wellness among such groups, studies emphasizing objective outcome measures while minimizing participant obligation to study protocols are ideal. Here, we discuss our experience studying a digital sleep intervention in a real-time setting and propose solutions for improving subject accrual, retention and methods for objective data collection in studies performed in a live shift worker population.