In the context of the boundaryless labor market, companies are increasingly considering the recruitment of former employees (“boomerangs”) as an alternative to traditional external new hires. Yet, research on the comparisons between boomerangs and new hires remains scant and yields inconsistent findings. Addressing these limitations and incongruencies, we comprehensively incorporate “time” into our theory-building process and propose that the impacts of boomerang status on four key behavioral outcomes (i.e., job performance, voluntary turnover, involuntary turnover, and turnback) unfold over time. Investigating 11,676 truck drivers in a large trucking company, we find that any initial boomerang advantages associated with job performance and involuntary turnover diminish over time. We also find that boomerangs are more likely to voluntarily leave and return for another employment term. Furthermore, our longitudinal employment data reveal that boomerangs who have returned multiple times (“serial boomerangs”) exhibit distinct behaviors compared to those who have returned only once. Finally, this research introduces two novel methodological approaches—the Fine-Gray subdistribution hazard model and the time-dependent moderation effect—to advance our understanding of survival analysis in the broad management literature.