Boomerang employees—individuals who return to an organization after leaving—are increasingly common. In this paper, we examine how boomerang mentors affect a critical aspect of their mentees’ career trajectories: mentees’ likelihood of departing from the organization. We hypothesize that boomerang mentors will increase mentees’ external mobility by reducing the perceived risk of leaving and providing valuable network ties, and that these effects will be stronger for women mentees. Using data from a large professional services firm which randomly matches mentors and mentees, we find that women are less likely than men to exhibit external mobility, but that boomerang mentors increase both men and women mentees’ likelihood of leaving. Further, we find that this latter effect is probably stronger for women; these gender differences are economically large but imprecisely estimated. Our work identifies both a contributor to and remedy for the persistent career outcome gap between men and women.