Utilising data from 10 semi-structured interviews (n = 5), this article explores the diplomatic challenges and concerns Canadian secondary teachers faced when teaching about political violence and the strategies they employed while navigating these. Drawing insight from the notion of 'everyday diplomacy', the article frames teaching as a kind of diplomatic practice, where teachers employ a variety of strategies, ranging from avoidance to forthright resistance, in response to interested actors' challenges and concerns. The findings also suggest the nature of these strategies depend on the teachers' teaching contexts and relations to interested actors, the perceived and/or real power of these interested actors' pressures, and the teachers' own professional maturity, and thus confidence in advocating for this type of professional work. My contribution is to offer insight into teachers' diplomatic knowledge, skills, and practices, and in doing so, highlight their importance as part of teachers' day to day professional work.