This study is an exploration of the relationship between subjectivity and pedagogy in the secondary school English classroom in South Africa during a time that can be characterised as one of considerable social change. It examines the subject positions students take up in relation to a teaching intervention that invites them to historicise their identities. In so doing, it seeks to contribute to the growing body of education research on how to meaningfully engage young people in post-conflict societies with their recent past and their shifting present, with the primary aim being to understand how these students are positioning themselves in relation to the changing sociopolitical context. The research was conducted in two Grade 11 English classrooms, one a de(re)segregated former Model C school and the other an elite private school. The research design is a two-case case study, employing ethnographic tools to generate a multi-layered and multifaceted understanding of the students’ engagement in all its forms. Poststructuralist theories on discourse and subjectivity form the theoretical framework for this study, informing both the methodology and the data analysis. At the heart of this lies Foucault’s notion of the discursively constructed subject, extended through the work of Stuart Hall, Chris Weedon, Bronwyn Davies and others in ways that facilitate their application to individual subjectivity, particularly in relation to the classroom as a pedagogically structured discursive space. The data is subjected to poststructuralist discourse analysis, adjusted to suit the mode and type of data which includes, inter alia, the analysis of a multimodal artefact, analysis of performative classroom talk and moment-by-moment analysis of classroom interaction. The analysis shows that students’ subjectivities are not fixed but shift in ways that are contingent on the pedagogic context. Such shifts are particularly noticeable when there is a shift in the interactional situation; when students move between different semiotic modes; or when they are provided with the opportunity for extended conversational interaction around an issue. In addition, students’ participation in the section of work on South Africa’s Truth and Reconciliation Commission (TRC) shows that engaging with the past in post-apartheid South African classrooms can have unpredictable results. Students’ resistance to engaging with recent history seems to be related to discomfort with the ways in which the grand narrative of the past works to position them in racialised ways. While there is evidence of students seeking to ‘unfix’ racialised subject positions, it is also clear that past discourses linger. Despite their desire to be rid of the past, students’ subject positions are frequently tied to their historically constructed locations in the sociopolitical and economic landscape of South Africa. These ambiguities and contradictions are viewed in part as a function of the complexity of the relationship between subjectivity and pedagogy, where what students are able to say and who they are able to be is shaped by the discursive structure of the classroom space. Ultimately it would seem that more serious consideration needs to be given to ways of developing a pedagogy that is able to tolerate contingency and heterogeneity and that would have relevance not only in post-conflict contexts but also beyond. Keywords: subjectivity, pedagogy, poststructuralist discourse analysis, positioning, identity, English classroom, TRC, multimodal artefact, classroom talk, South Africa