This chapter outlines “system-challenging” praxis in DEI and potential mechanisms for implementing radical and permanent structural changes within university environments. There are no standardized solutions for DEI and while higher education institutions may share some common DEI challenges, specific issues need to be identified through quantitative and qualitative data gathering activities and tailored actions produced. An essential component is to create, embed and disperse accountability to meet these goals. DEI initiatives that rest on the shoulders of a few passionate (often overworked) staff will generally fail because this approach sequesters responsibility and does not address the fundamental structural issues. This chapter provides practical guidance on how to move forward, even in the face of resistance to any change to the status quo. The chapter is important for re-envisioning higher education as a form of resistance against conservative, neoliberal systems and structures using radical system-challenging praxis.