This chapter explores how the individual outcomes of study abroad contribute to the contemporary transnational role of study abroad. The empirical findings of a retrospective mixed-method study on US study abroad in Japan from the 1960s to 2010s provide a basis of understanding the role of study abroad in promoting transnational awareness and connectivity for knowledge diplomacy through a multidimensional process that focuses on participants' subsequent academic, professional, and academic development. Through tracing the life experiences of 50 years of study abroad participants, the conceptual model suggests that participants form a lifelong connection with Japan and the wider world. Moreover, Japan also acts as a gateway to the host region of Asia. The model acknowledges the role of historical markers, namely political, social, cultural, and economic, as shaping individual outcomes. Study abroad provides a disruptive awakening through conscientization and transformative learning that contribute to knowledge diplomacy by promoting a greater awareness of participants' positionality within the wider world and the desire to understand and critically engage in their subsequent life trajectories across national borders and sociocultural terrains.