In March of 2011 Unite States president Barack Obama announced the "100,000 strong in the Americas" program during his visit to Chile (U.S. State Department, 2011). The initiative's goal is to reach 100,000 U.S. students studying in Latin America and 100,000 Latin American students studying in the United States. This interchange of students, knowledge, and ideas is viewed as a positive way to increase understanding between the two regions by means of building interpersonal ties between students who are billed as future leaders. Scholars in the intercultural relations and study abroad literature describe educational exchange between countries as an activity that instills tolerance in those who participate while converting them into potential bridges between cultures (Cushner & Karim, 2004). Furthermore, a plethora of studies illustrate the positive personal transformations that students undergo while learning in different countries and cultures (Hadis, 2005). Thus, Obama's proposal for improving the often strained geo-political relationships between the regions through interpersonal contact is encouraging to say the least. However, as with any picture perfect plan there are potential flaws and caveats that policy makers must consider before declaring victory. The goal of this research is to examine the foremost problem underlying this student exchange plan and undermining its potential to build intercultural understanding.