This article explores the transition experiences of ten South Korean students who first studied in the United States within the community college setting and who viewed their transition experience as successful through an original grounded theory study. Interviews were recorded, transcribed, and analyzed, resulting in the emergence of a grounded theory. This theory revealed five main categories: one context category and four subsequent developmental stages of challenge, reflection, action, and growth. Challenge emerged as the central category due to its pivotal role in participants’ ultimate experiences of a successful transition. In particular, the process following the point of encountering challenges set in motion a set of decisions through which participants navigated their difficulties by utilizing personal and cultural skills. Many of these skills were unique to the South Korean population. Utilizing these skills and attributes, participants reported developing the strength to manage with diligence and ultimately gain the confidence to do more on campus and in their larger communities. The process of self-reflection, self-awareness, and confidence-building plays a key role in these experiences of success. The findings identify stressors linked to critical challenges that South Korean international students face and describe how some South Korean students successfully navigate those challenges. These findings are relevant to student services personnel and college counselors who support South Korean international students in higher education.