Applying Culture and Appreciative Education lenses, this qualitative study, eliciting detailed descriptions, examines six North American adult and higher education scholars' lived learning experiences and insights gained from their academic collaborations in and with the East. Our findings indicate that participants hold unique international collaboration experiences with commonalities. Most participants experienced language and cultural barriers in real-time, on-site collaborations that they would not have considered otherwise without these experiences. Many differences made them realize the fundamentals for intercultural collaborations. They consciously learned to reposition with appreciative mindsets and co-construct goals and solutions with counterparts. All participants indicated that transnational contexts enable profound reflective and authentic learning, renewed understandings of cross-cultural sensitivity, and different ways of thinking and doing. This study demonstrates that international collaborations promote adult learning with self-awareness for a new dimension of global learning and cultural competency in the internationalization of adult education.