This chapter constitutes a comparative analysis of the transitional periods that have followed each of Sudan’s post-independence uprisings, including the 1964 October Revolution, 1985 April Intifada, and 2018–2019 Sudanese Revolution. It assesses the role of both the military and rebel groups in each of these interim periods, in addition to the role of the Rapid Support Forces militia in the present transition, asking why the current transitional regime has broken down in spite of being the first to sign a peace deal with rebels in the marginalised regions. It contends that the immediate failure of the contemporary transition, as well as the long-term failures of past transitions, should be understood in the context of their inability to overcome the divides between the centres and peripheries of Sudanese society and the Sudanese body politic. This has enabled authoritarian actors that thrive off that divide to undermine the transition to a mass-based country-wide democracy and maintain a violent and extractive economy that continued to generate conflict in the marginalised regions and subsequent to 2023 those of the riverain centre.