Today’s college student body reflects, among many things, the outcome of policies geared towards increasing access and diversifying the academy, efforts to recruit international students, the vast social, political, and economic disparities among marginalized populations, and the extreme cultural polarization of our times. Students on campuses have broad and individualized perspective, approaches, and values, which are culturally rooted, embedded within our socialization and often times conflict with the experiences of other students or the student affairs professionals tasked with supporting students. Student affairs practitioners must enter the field possessing a degree of intercultural competence, defined as an appropriate skillset and mindset, to effectively work across difference and support today’s college student. While the development of intercultural competence is a life-long learning process, master’s-level preparatory programs serve as a critical space for aspiring student affairs practitioners to engage in intercultural learning and skill development. Utilizing pre and post data result from the Intercultural Development Inventory and information gathered from post-graduation interviews, this mixed-methods study examined the intercultural competence development of students in Higher Education within a student affairs master’s level preparatory and their intercultural learning experiences at the assistantship site. The study found that across assistantship sites and observed developmental change, intercultural learning was dictated by the three themes: influential relationships, impactful factors, and depth of engagement.