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Advance Care Planning (ACP) has long been a staple of caring for people with serious illness. To better understand the challenges and opportunities for ACP, acknowledge and highlight divergent viewpoints, and examine what is empirically known and not known about ACP and its outcomes, the National Academies of Sciences, Engineering, and Medicine's Roundtable on Quality Care for People with Serious Illness hosted a virtual public workshop. The workshop explored the paradox of ACP, its evidence base, ways to think differently about ACP, and various approaches to making it more effective. This Proceedings of a Workshop summarizes the presentations and discussions from that workshop.