The longstanding practice of observing two-day Jewish festivals (Yom Tov Sheni) faces mounting pressure within American Conservative Judaism, yet abandoning it could fracture congregations and eliminate second-day observance within two generations. While the 1963 Committee endorsed continued study rather than elimination, subsequent proposals by Rabbis Sigal and Ehrlich advocated aligning with Israeli single-day observance. Analysis of committee deliberations, congregational surveys, and halakhic precedent reveals that although Jewish law permits multiple interpretations, the paramount consideration must be Judaism's future vitality. A nuanced solution emerges: allowing single-day observance only for congregations facing severe difficulties while maintaining the two-day tradition elsewhere. Rather than defaulting to elimination, creative experimentation can enhance Yom Tov Sheni's meaning, leveraging these additional festival days as crucial opportunities for spiritual growth and family connection in modern American Jewish life.