This article contributes to the body of research addressing the challenges of expatriate teaching appointments. It is written in the form of a critical incident analysis. Rather than focus the lens of concern on the preparedness, adaptability, and potential culture shock of the teacher who travels into an unfamiliar work context, postcolonial theory is used to focus on the knowledge-power dynamics that come into play when Western teachers take up positions in once-colonised countries of lower economic status than the teacher's home country.