The chapter discusses the important role that repatriation plays in career development or an international assignee’s personal and professional career outcomes acquired, developed, and accumulated over time. Attention is devoted to understanding how different types of career resources and competencies, categorized as “knowing how”, “knowing whom”, and “knowing why”, are developed as a function of living and working in another country. The chapter continues by drawing on the traditional bounded and emerging proactive career perspectives to help us understand why returning home is often more complex and difficult than perceived. Next, the chapter examines repatriation “success” from both the organizational and the individual repatriate’s points of view, highlighting objective and subjective interpretations of career success. The chapter concludes with a discussion of the challenges facing the repatriation process at the individual-, team-, organizational-, and country-levels and suggests interventions that could be considered in an effort to improve the likelihood of repatriation success. Implications for future research are also discussed.