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Background: In the modern economy, shift work is prevalent in numerous occupations. However, it often disrupts workers’ circadian rhythms and can result in shift work sleep disorder. Proper management of shift work sleep disorder involves comprehensive and patient-specific strategies, some of which are similar to cognitive behavioral therapy for insomnia. Objective: Our goal was to develop and evaluate machine learning algorithms that predict physicians’ sleep advice using wearable and survey data. We developed a web- and app-based system to provide individualized sleep and behavior advice based on cognitive behavioral therapy for insomnia for shift workers. Methods: Data were collected for 5 weeks from shift workers (N=61) in the intensive care unit at 2 hospitals in Japan. The data comprised 3 modalities: Fitbit data, survey data, and sleep advice. After the first week of enrollment, physicians reviewed Fitbit and survey data to provide sleep advice and selected 1 to 5 messages from a list of 23 options. We handcrafted physiological and behavioral features from the raw data and identified clusters of participants with similar characteristics using hierarchical clustering. We explored 3 models (random forest, light gradient-boosting machine, and CatBoost) and 3 data-balancing approaches (no balancing, random oversampling, and synthetic minority oversampling technique) to predict selections for the 7 most frequent advice messages related to bedroom brightness, smartphone use, and nap and sleep duration. We tested our predictions under participant-dependent and participant-independent settings and analyzed the most important features for prediction using permutation importance and Shapley additive explanations. Results: We found that the clusters were distinguished by work shifts and behavioral patterns. For example, one cluster had days with low sleep duration and the lowest sleep quality when there was a day shift on the day before and a midnight shift on the current day. Our advice prediction models achieved a higher area under the precision-recall curve than the baseline in all settings. The performance differences were statistically significant (P

CBT for Insomnia: Better Sleep, Better Mind - How to Improve Sleep and Reduce Nighttime Anxiety Cognitive Behavioral Therapy or CBT is not new, but there are