Many studies on the consequences of training have shown that training generally reduces turnover. However, some employees who receive training support from their firms are likely to leave, resulting in the outflow of valuable human capital resources. This study examines this paradoxical phenomenon, referred to as the "training dilemma." To better understand the firm-level risks associated with training, we hypothesize that the effects of training on voluntary turnover vary depending on occupational types (e.g., white- and blue-collar jobs), firm size, and benefit options. These hypotheses draw on literature addressing (1) employee poaching and (2) employee mobility and career success. Specifically, we investigate whether the training dilemma is more pronounced among white-collar workers compared to blue-collar workers. Additionally, we identify firm size as a contextual factor that may intensify the training dilemma. Furthermore, we explore how employee benefits could mitigate the positive relationship between training and voluntary turnover. Our multilevel analyses, conducted on data from 229 South Korean firms in the Human Capital Corporate Panel (HCCP) spanning 2009 to 2017, support our hypotheses. We discuss the implications of the varying nature of the training dilemma as a function of occupational types, firm size, and employee benefits.