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Background and Objectives A substantial portion of the service sector workforce is middle-aged or older, but little is known about the scheduling conditions of these older workers. This study describes the quality of work schedules in the service sector by age and tests associations of unpredictable schedules with well-being and job retention among workers ages 50-80. Research Design and Methods The Shift Project collected survey data on detailed working conditions and health from 121,408 service sector workers, recruited in 2017-2020 using social media advertisements. Survey weights aligned sample demographics with the American Community Survey, and multiple imputation addressed missingness. Ordinary least squares regression models were used to examine associations between age and schedule stability, and ordinary least squares, ordinal logit, and logit regression models tested associations between schedule stability and well-being and job retention outcomes for older workers. Results Scheduling conditions were more stable and predictable for older compared to younger workers; however, more than 80% of workers ages 50-80 experienced one or more types of routine schedule instability. Among workers ages 50-80, unpredictable schedules were associated with psychological distress, poor-quality sleep, work-family conflict, economic insecurity, job dissatisfaction, and intentions to look for a new job. Canceled and back-to-back closing and opening ("clopening") shifts were most strongly associated with negative outcomes. Discussion and Implications Policies aimed at improving scheduling conditions hold promise to benefit older service workers’ well-being. As the population ages, improving work schedules in the years approaching retirement may be important to longer working lives.