Applying the Strategic Relational Approach, this paper analyses the circumstances behind and educators' strategies in response to education reforms in two nation-states undergoing socio-political transformation--Bolivia and Timor-Leste. Despite the starkly different histories and contemporary context of each nation, we suggest that transformation in both settings is driven by a desire to unshackle histories of colonisation and social conflict. Education reform, at least discursively, aims to dislocate past practices and replace them with a new material reality. In such spaces, we find that teachers are acting as strategic political actors, but in ways that are historically situated and driven by real and perceived personal and professional constraints. Their actions lead to particular types of "resistance" and strategic action, leading to outcomes that are simultaneously continuous and disconnected from the past.