Current U.S. government space systems acquisition processes are regularly criticized for their inability to adequately plan for the frequent cost overruns and schedule delays experienced by new developments and acquisitions. These overruns and delays can have a detrimental effect across a portfolio of projects and programs leading to reduced integrated capabilities and delayed fulfillment of critical requirements. Although best practices for improved cost and schedule estimating are continually being pursued, the natural tension between conservative estimating and aggressive planning will always exist to avoid the ever-present fear of being dubbed a "non-starter" and cancelled early in a project's lifecycle. Thus, portfolio planning across an enterprise of projects and Programs must address the uncertainty that exists within new acquisitions in an environment of ever-changing stakeholder needs and strategic, economic, and political priorities while demonstrating the value of each investment to the enterprise strategic vision. Existing portfolio management processes are often disconnected from strategic plans and focus solely on the static affordability of an existing portfolio, disregarding the executability and sustainability of these programs in the dynamic, high risk environment of space systems acquisition. This paper proposes a process to improve enterprise portfolio planning through the integrated evaluation of five critical metrics: Capability, Affordability, Executability, Adaptability, and Continuity. These five metrics, referred to as the Five Pillars of Enterprise Portfolio Planning, are critical components for optimizing the portfolio management process, which is all the more important in a current environment emphasizing the need for resilient enterprise architectures whose successful implementation will require accounting for both programmatic and operational threats. The first metric, Capability, quantifies the alignment between a portfolio of functio
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