The notion of transformation is gaining traction in contemporary sustainability debates. New ways of theorising and supporting transformations are emerging and, so the argument goes, opening exciting spaces to (re)imagine and (re)structure radically different futures. Yet, questions remain about how the term is being translated from an academic concept into an assemblage of normative policies and practices, and how this process might shape social, political, and environmental change. Motivated by these questions, we identify five latent risks associated with discourse that frames transformation as apolitical and/or inevitable. We refer to these risks as the dark side of transformation. While we cannot predict the future of radical transformations towards sustainability, we suggest that scientists, policymakers, and practitioners need to consider such change in more inherently plural and political ways.