This study probes the limits and possibilities of US military efforts to facilitate the transition from warfighting to nation-building. Most comparative studies conceive the complexity of this transition along a spectrum from conflict to humanitarian assistance to post-conflict stabilization. While the last two stages have often been interpreted as a coordinated act of civil-military ‘nation-building’; the spectrum, in fact, represents an ideal type simplification. At one level, outcomes depend on the players involved, including: sovereign nations, national militaries, international and regional institutions, UN peacekeepers, private security contractors, and non-governmental humanitarian providers, among others. On the other hand, because the number, types, and causes of case outcomes are highly diverse and contingent upon many possible factors (among them for example: political, economic, military, organizational, humanitarian, cultural, and religious), institutions like the US military face serious difficulties both planning and coordinating post-conflict scenarios. Assuming this complex backdrop, the present study offers a qualitative analysis of two recent US government reports by the Special Inspector General for Afghanistan Reconstruction (SIGAR) and the Special Inspector General for Iraq Reconstruction (SIGIR) on US military engagement in Afghanistan and Iraq. In both cases, the US government sought to ‘nation-build’ by facilitating post-war stabilization and humanitarian assistance, detailing its genuine efforts to record both processes. While results indicate some limited successes in both cases, they also indicate a familiar pattern of uneven performance failures consistent with other cases internationally. The analysis concludes with recommendations for further research that may better control the contingencies of post-conflict management.