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Objectives: The aim of the present study was to assess both the direct and indirect effects (i.e., interacting with various job demands) of skill discretion on various psychological outcomes (i.e., emotional exhaustion, intention to leave, affective well-being, and job satisfaction). Material and Methods: Data were collected by a self-reported questionnaire in 3 hospitals in Italy. The sample consisted of 522 nurses. Moderated hierarchical regression analyses were employed. Results: The findings highlighted the direct effect of skill discretion on reducing emotional exhaustion, intention to leave, sustaining affective well-being and job satisfaction. As regards interaction effect, the analyses indicated that skill discretion moderates the negative effect of disproportionate patient expectations on all the considered psychological outcomes. On the other hand, skill discretion was found to moderate the effect of cognitive demands on turnover intention as well as the effect of quantitative demands on emotional exhaustion and job satisfaction only in conditions of low job demands. Conclusions: The study revealed some interesting findings, suggesting that skill discretion is not a resource in the pure sense, but that it also has some characteristics of a job demand. The study has relevant practical implications. Particularly, from a job design point of view, the present study suggests that job demands and skill discretion should be balanced carefully in order to sustain job well-being and worker retention.