Shulchan Aruch: Chapter 599 - Recitation of the Passage VaTodieinu on Rosh HaShanah

This law is applicable only with regard to the second day of Rosh HaShanah. Rosh HaShanah can never begin on Saturday night, for according to the fixed calendar we follow, the first day of Rosh HaShanah can never fall on Sunday.

The problematic linkage of “the celebration of the pilgrim festival” to Rosh HaShanah is not new. Ravia, the medieval author of Avi HaEzri, writes that when he confronted his mentors with this anomaly he was told: When any other festival ends on a weekday, the blessing of separation nevertheless speaks of the distinction “between the Seventh Day and the six workdays” — because we say that the passage is simply enumerating a series of separations (Chullin 26b). In the same way, he was told, the standard wording of VaTodieinu simply enumerates the series of festivals that were ordained for us. (See: Piskei HaRosh, sec. 14, on Rosh HaShanah, ch. 4; Tur, sec. 599:1. Characteristically, the Alter Rebbe’s original phrase (seder hatikkun — hamatanos) interweaves elements from all the above-mentioned sources.)

Lit., “separation.” In this case, the blessing of Havdalah demarcates the superior sanctity of the departing Shabbos from the lesser sanctity of [the incoming second day of] Rosh HaShanah. Thus, instead of concluding with the usual weekly wording, hamavdil bein kodesh lechol, blessing the One “Who makes a distinction between holy and ordinary,” the different version on this occasion concludes, hamavdil bein kodesh lekodesh, blessing the One “Who makes a distinction between holy and holy.”