For the last couple of decades, a dominant trend has emerged within decentralization scholarship that has shifted focus away from the reform process as a development, governance (re)constructive process, and post-conflict management tool, and towards the litany of empirical data arguing for and against the approach. Despite the theoretical benefits of decentralization accentuating the probable benefits applied to post-conflict conditions, scholarship has largely noted the dangers conceivably emergent from a faulty application of decentralization and the noted empirical benefits to service delivery. In lieu of this the paper pursues on the basis of decentralizations possible benefits in the stabilization and pacification of post-conflict heterogenous states within Africa, an inquiry into why states are enabled to succeed and fail in the decentralization of their provision of health. We propose and set up a comparative analysis centred on two similar cases: Sierra Leone and Rwanda. The former is identified as an unsuccessful case of decentralization, while the later as a successful one. The paper thusly formulates an inquiry into the variance in our outcome of interest and in that endeavour constructs a theoretical framework rooted in a historical institutionalism and informed by Falleti’s theory of sequential decentralization and path dependency. From these the thesis posits that (un)successful decentralization of health occurs primarily on the basis of specific path dependent sequence patterns and/or the from the effect that the initial design of the decentralization types: administrative, fiscal, and political have on overall process. The analysis and comparative examination discovers that (un)successful decentralization of healthcare lay rooted specifically in the design of the initial two reform types and form the willingness of the central government to pursue and entrench decentralization reforms.