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The decision about whether to participate in the Centers for Medicare and Medicaid Services’ (CMS’s) new Medicare Shared Savings Program (MSSP), Pathways to Success, is complicated. It requires a detailed understanding of the rules of the program, your patient population, as well as your level of maturity with several key population-management capabilities (e.g., care management, analytics, and clinical redesign). These requirements raise a few questions and present challenges for current MSSP participants in upside-only arrangements and for new entrants considering joining the program. One of the most significant challenges is the requirement to take on downside risk much earlier in the program.