Existing research on history education’s role in agendas of transitional justice is focused on societies undertaking regime change or rebuilding after extensive conflict and often centres disciplinary competencies as part of educational reform objectives to support political transition. However, the orientation towards transitional justice in settler colonial democracies such as Australia has prompted debate about the role of history curriculum in transitional contexts where constructivist, discipline-based approaches are already prescribed. While “historical thinking” in Australia has been a pragmatic middle way between polarised single-narrative and deconstructivist paradigms, this article argues that questions of transitional justice return the subjective, contemporary, and political to history education in ways that challenge the scope of disciplinary meaning-making and complicate the civic promises of disciplinary thinking. By discussing examples of how time is presently imagined and engaged using second-order historical thinking concepts, this article engages some key limitations of disciplinary history curriculum vis-à-vis transitional justice. It suggests alternate approaches that stretch the disciplinary paradigm in new directions that carry important implications for other societies engaged in questions of transitional justice.