This collaborative self-study details the experiences of an Australian teacher educator and a Canadian teacher educator, who led teacher candidates on international practicum placements to the Cook Islands and Kenya respectively. Focusing on critical incidents, they collaboratively analyzed dilemmas that occurred when providing professional development sessions for local teachers during these placements. These dilemmas required the teacher educators to think deeply about their beliefs and practices in these contexts. Findings from the study included the teacher educator's tendency to make assumptions about good teaching and learning practices that were reflective of their personal pedagogical values and beliefs; their discomfort with their perceptions of some neo-colonial practices within these international practicum sites and uncertainty about how to navigate the resultant tensions; and, the need to view the work of teacher educators though a new cultural lens when working in transnational contexts. Implications for teacher educators working with local hosting teachers during international placements include the need to understand and acknowledge the complexity of this dimension of teacher educators' work, and for teacher educators to engage in parallel learning journeys with the teacher candidates they accompany. This involves critically reflecting on the experiences, assumptions, and beliefs that they bring to their new contexts, as well as adopting a global perspective and a deep consciousness of how one is perceived by others who are culturally, racially, or linguistically different.