This article draws on and contributes to the body of knowledge on the development of cultural competence and study abroad experiences. The study program has been well established for several years and blends a 12-day intercultural immersion experience with preparatory classroom teaching and relevant assessment. This study builds on an earlier evaluation, adopting a robust qualitative approach. The study confirms that such experiences can significantly contribute to transformation in students’ capacity to challenge superficial cultural stereotypes and critically engage in the interplay among disadvantage, contextual factors, and sociopolitical structures. Developing critical reflection skills is an integral component in promoting transformation.