For practicing and non-practicing Jews (and allies) alike, Yom Kippur presents an invitation and a challenge. On the one hand, it is very widely observed -- often with family -- and invites a kind of introspection familiar to lovers of the Dharma. On the other hand, Yom Kippur can be profoundly alienating in its approach to ethical refinement, its theistic liturgy, and its contemporary cultural trappings. In this session, Jay Michaelson explores some Dharmic practices, texts, and wisdom for making the most of this "retreat of retreats" (Shabbat Shabbaton).