Research on mentoring programs has portrayed them almost exclusively beneficial for newcomer retention. Drawing from the social cognitive model of career management and the boundaryless career perspective, we depart from this predominant view and examine the “double-edged sword” effects of career support mentoring on newcomer turnover. We propose that career support mentoring received by newcomers is likely to elicit both internal proactive socialization and external career self-management, which act as countervailing forces driving newcomer turnover in opposite directions (i.e., the retention pathway and the unintended detrimental pathway). We further propose that the organizational role of the mentor—supervisor versus nonsupervisor—is critical in determining which pathway prevails. We conducted two multiwave newcomer studies to test our hypotheses. In Study 1 (N = 495), we found that received career support mentoring was associated with lower newcomer turnover probability through the serial mediation of internal proactive socialization and perceived internal marketability but higher newcomer turnover probability through the serial mediation of external career self-management and perceived external marketability. In Study 2 (N = 193), we found that received career support mentoring was associated with lower newcomer turnover intention through the serial mediation of internal career advancement expectation and internal proactive socialization but higher newcomer turnover intention through the serial mediation of external career advancement expectation and external career self-management. In both studies, the unintended detrimental pathway was significant only when a newcomer’s mentor was not a supervisor.