This chapter summarizes and further develops a growing body of literature that has begun to present and critically investigate, through a sociological lens, the emergent pathways to university from well-established accredited private K-12 English-medium “elite traditional international schools” (ETIS) in East Asia that are authorized by the International Baccalaureate (IB) to deliver the Diploma Programme (IBDP). It is not uncommon for the ETIS to send their IBDP graduates, over a 5-year period, to upward of 180 universities in 20 different nations. However, in recent years, it has become clear that a phenomenon has emerged whereby a disproportionate amount of graduates are traveling together toward the same few destinations. A distinct clustering trend can be observed involving five universities in four global cities (London, New York, Toronto, and Vancouver). Studies using university matriculation has revealed that a “Big-5” are attracting an average of 11–15% of all graduates. Sometimes, in East Asia in particular, that proportion is even higher. Having firmly identified and presented the clustering trend, the literature base is now ready for making sense of it as well as furthering developing the contradictions and paradoxes. One way forward involves the viewing of the clustering trend being the preferred pathway of a newer “global middle class” in East Asia with cosmopolitan sensibilities seeking to forge an alternative pathway into the global labor market. A further lens of inquiry would involve identifying the secluded and segregated ETIS in East Asia acting as incubators and carriers of IBDP graduates, toward universities that are deliberating formulating a cosmopolitan stance.