When ancient rabbis established a second festival day for Diaspora Jews uncertain about the lunar calendar, they likely never imagined their emergency measure would persist into the age of instant global communication. A landmark responsum by Rabbis Philip Sigal and Abraham J. Ehrlich challenges the continued mandatory observance of Yom Tov Sheni Shel Galuyot (second festival days), revealing through careful analysis of Talmudic sources, medieval commentaries, and contemporary rabbinic opinions that these additional days may now be treated as regular weekdays or Chol Hamoed. Through systematic examination of primary sources including Maimonides, Rashi, and the Shulchan Arukh, the authors demonstrate that leading authorities historically viewed the second day as custom (minhag) rather than permanent legislation, with limited inherent sanctity. Modern circumstances—reliable communication systems, fixed calendar knowledge, and practical hardships in Western societies—have effectively nullified the original rationale for these observances. The research establishes halakhic precedent supporting optional observance of Yom Tov Sheni, enabling individual congregations to adopt the Israeli liturgical calendar while maintaining traditional observance of biblically mandated first days. This finding offers a path forward amid educational conflicts and declining observance rates, potentially strengthening Jewish unity between Israel and Diaspora communities.