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Work in out-of-school learning programs can be stressful, and job stress may have cascading effects for the children and youth that attend. Fortunately, workplace supports can help decrease this stress. In this study, we aimed to understand how youth workers’ personal and work-related demands as well as supports predict on-the-job stress. We used multilevel modeling to investigate the demands and supports of a sample of 111 youth workers nested in 25 programs. Results suggested that job stress systematically varies at the program level. We found that stress at home and a negative staffing climate is associated with higher stress and the presence of supervisor support is associated with lower staff stress. Supervisor support, in particular, likely can play a key role in decreasing youth worker stress. We discuss implications for training supervisors and structuring programs to support staff and to ultimately foster more positive out-of-school program experiences for the children and youth that attend.