Teacher professional development has undergone a paradigm shift over the past thirty years– from unidirectional acquisition of knowledge and skills to situated learning. This shift has brought attention to the influence of contextual factors on teacher professional development. In recent years, increasing attention has been paid to personal factors and school context on teacher development; however, research on cross-border teacher professional development remains relatively scarce. Given Taiwan’s long-standing commitment to enhancing the professional development of teachers in Malaysian Chinese independent high schools, this study employs the cultural-historical activity theory to conduct an in-depth analysis of the contradictions and transformations within the transnational teacher professional development system between Taiwan and Malaysia, aiming to understand the needs and underlying causes influencing teacher professional development. The study employs individual interviews, focus group discussions, and document analysis to collect data. Findings reveal that transnational teacher professional development faces multi-level contradictions during its implementation: (1) First-level contradictions arise within the system’s rules and division of labor, such as constraints on training participation and heavy workload responsibilities; (2) Second-level contradictions occur among system elements, particularly between division of labor and objectives, reflecting inconsistencies between teachers’ and administrative units’ goals and needs; (3) Third-level contradictions stem from the transition between old and new systems, particularly the conflict between exam-oriented education and innovative pedagogy; (4) Fourth-level contradictions exist between the core professional development system and the broader educational systems of Taiwanese and Malaysian Chinese independent schools. Despite these challenges, some schools and teachers have undertaken transformative actions that support the implementation of professional development. This study highlights the complexity of transnational teacher professional development and underscores the importance of multi-level collaboration, offering insights for international education policy and practice.