This review paper focuses on answering 2 research questions: (a) Does transformational leadership predict employee well-being? (b) If so, how and when does this prediction occur? A systematic computerized search and review of empirical papers published between January 1980 and December 2015 was conducted. Forty papers were found that met the criteria of reporting empirical results, being published in English, and focused on answering the above research questions. Based on these papers it appears that, in general, transformational leadership positively predicts positive measures of well-being, and negatively predicts negative measures of well-being (i.e., ill-being). However, recent findings suggest that this is not always such a simple relationship. In addition, several mediating variables have been established, demonstrating that in many cases there is an indirect effect of transformational leadership on employee well-being. Although some boundary conditions have been examined, more research is needed on moderators. The review demonstrated the importance of moving forward in this area with stronger research designs to determine causality, specifying the outcome variable of interest, investigating the dimensions of transformational leadership separately, and testing more complicated relationships.