This chapter looks at public sector whole-of-government reform from an Information Technology (IT) focused Enterprise Architecture (EA) perspective. The chapter summarizes reforms undertaken under three US presidents—Clinton, Bush, and Obama—and discusses how they have too frequently failed to meet expectations of policy makers, public servants, the public, and other stakeholders. We find that IT reforms in support of larger public sector reform have been ineffective and unsustainable, although many IT reforms have been successful in a narrower context. EA has suffered as a once promising methodology: it has not become the “silver bullet” in managing the IT and information infrastructure to support reform, knowledge management, and decision making. It was also seen as an important tool for reducing information management silos that successive governments have unsuccessfully tried to reduce. This chapter raises the spectre of endemic barriers to reform that must be overcome if EA and IT reform are to realize their potential, and offers recommendations for overcoming these hurdles in the context of whole-of-government public sector reforms.