The chapter starts by providing introductory perspective on how the risk modeling and analysis needs for strategic portfolio planning differ from those for system design, development, and operation, in terms of the relative degree of reliance on quantitative vs. qualitative techniques. It then provides a review of the methodology used by NASA’s Review of Human Spaceflight Committee (led by former Lockheed-Martin CEO Norman Augustine) to assess alternative human spacecraft programs for NASA, and extends that methodology to apply to the risk-informed selection of a comprehensive portfolio of programs. In doing so, it introduces the concept of benefit significance scores as measures of opportunity for aspirational enterprise objectives (e.g., community involvement, technology transfer, etc.), and provides examples of how to conduct elicitations of high-level planning authorities to quantify the benefit significance scores and to determine associated risk tolerance levels and risk acceptance levels. It also illustrates how the Monte Carlo analysis for assessing the aggregate risks in individual programs may be expanded to apply to enterprise-level program portfolios containing multiple program elements and various types of objectives. It ends by demonstrating the use of spider charts to display the resulting risk and opportunity posture for each candidate strategic portfolio in a management friendly format.