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Introduction: Older Chinese Americans often defer end-of-life care discussions. Researchers sought to explore how to engage older Chinese Americans and their families in end-of-life care discussions and to understand the optimal timing to initiate such discussions. Methods: Individual, semistructured interviews were conducted with 14 community-dwelling older Chinese Americans, 9 adult children, and 7 clinicians. The data were collected and analyzed using focused ethnographic methodology. Results: Older Chinese Americans and their families would discuss end-of-life care when introduced at “optimal times,” which included after-triggering events (e.g., death of loved ones, fall accidents), changes in health status, or advanced age. Discussion: Adult children are not expected to initiate end-of-life care discussions with their parents. Thus, culturally congruent health care that could better engage Chinese Americans in such discussions would be optimized by having clinicians proactively assess their patients’ readiness and initiate such discussion at optimal times.