Teachers who teach in cross-cultural settings play a vital role in nurturing students' appreciation of cultural diversity but they tend to experience tremendous challenges in their early years of teaching. To draw a dynamic portrayal of those challenges, this study primarily collected and analyzed 521 reflective journals written by 14 Chinese language teachers throughout their first 2 years of teaching in U.S. public schools. The study found that the teachers experienced a wide range of challenges in managing classrooms, developing curricular materials, crafting instructional strategies, assessing students, catering to learner differences, and collaborating with others. The seriousness of the challenges varied across areas and transformed differently over time. Cultural difference, school context, and teacher's background and ongoing learning collectively contributed to the formation and transformation of the challenges. This paper concludes with practical implications on how to prepare and support teachers to work in cross-cultural settings.