The international community has long relied on United Nations (UN) peace operations as the means of creating and maintaining international peace and security, however the realities of what a “successful” mission looks like remains obscured, as the experiences and definitions of success may differ between the various players involved. While a shared definition of success and operational structure remains elusive, it is clear that the assessment of UN missions must be conducted in a holistic manner, from mandate crafting, to mission transition and exit. Among these realities is that the assessment of UN peace operation success is all too often hindered by political partiality with the determination of mission success frequently held hostage by faulty political processes. It is essential that evaluative frameworks encompass the various stages of a peace operation, in order to illustrate the political challenges that often obstruct the planning and assessment of a UN mission. Highlighting the political obstacles associated with holistic mission planning and assessment, against the backdrop of ongoing, ad hoc UN peace operation deployments to Haiti, breaks down existing normative positions and exposes the realities and voids in current methodology.