This chapter focuses on the ambiguities surrounding the beginning of Sabbath and festivals in ancient Jewish sources, assumed to take place sometime in the evening but difficult to pinpoint. After a discussion of ancient Jewish approaches to the notion of “evening,” particularly the phrase “between the two evenings” mentioned as a time for certain sacrifices in the Pentateuch, the chapter investigates how ancient Jews handled the difficulties of establishing the precise beginning of Sabbath and festivals. It is shown that Jews up to the early rabbinic period responded with two approaches, thereby “bracketing” the start of day: some required an early start of rest, whereby time prior to the day was invested with appropriate behavior, while others spent the beginning of Sabbath and festivals at common meals, transitioning into the holy day under the controlled inertia of being seated at table and performing short rituals on account of the sanctity of the day. Only later do we find obligatory evening prayer for which Jews gathered in synagogues, as well as more detailed, experience-based attempts at establishing the beginning of the day more precisely.