Chapter 3 examines how the transformative powers of global learning increase or decrease when students make use of the organizational structures of academic programs, support services and funding schemes at pre-college and college levels. The chapter examines mass higher education-related inequalities that emerge at various universities, which have different stances on the ability of students to break boundaries, disrupt educational conventions and juxtapose cultures to facilitate better understanding of differences in social and institutional learning environments. While some students take bold actions to dismantle conventions or challenge dogmas, others approach adverse environments and circumstances with patience, often to the disadvantage of their own progress in global learning. The cross-cultural investigations of the institutional structures are illustrated by the participants in a critical manner. Amidst these explorations, the institutional agency emerges as a complex and sometimes incompetent facilitator of people’s needs and expectations.