Question: Regarding the “Leeshev Ba’Sukkah” blessing, what is more halachically preferable: To recite the blessing while standing before sitting down to begin one’s meal in the Sukkah or should one recite this blessing when he is already seated after having recited the Hamotzi blessing on the bread?
Answer: During the night and day of the first day of Sukkot (the first two days outside of Israel) and on the Shabbat which coincides with Sukkot when the “Leeshev Ba’Sukkah” blessing is recited in the Kiddush, one should recite the “Leeshev Ba’Sukkah” blessing at the end of the Kiddush after which one should sit down and drink some of the wine. (On the first night of Sukkot, the “Shehecheyanu” blessing is recited after the “Leeshev Ba’Sukkah” blessing, i.e. after reciting the “Leeshev Ba’Sukkah” blessing, one should be seated, recite the “Shehecheyanu” blessing, and drink some of the wine.) Our question applies to the other days of Sukkot when Kiddush is not recited as some people have the custom to recite this blessing after the Hamotzi blessing when they are already seated while others customarily recite the blessing when they enter the Sukkah (after having washed their hands for eating a bread meal) while they are still standing and after reciting the “Leeshev Ba’Sukkah” blessing they sit down, recite the Hamotzi blessing and begin eating.
Indeed, the Maharam of Rottenberg followed the latter custom of reciting the “Leeshev Ba’Sukkah” blessing while standing before sitting down to recite the Hamotzi blessing as this seems to be the implication of the Baraita (Sukkah 46a) which states, “When one enters the Sukkah to sit in it, one recite the ‘Leeshev Ba’Sukkah’ blessing.” This implies that one should recite the blessing while he is still standing and only then be seated and recite the Hamotzi blessing. Additionally, when one recites the blessing in this way before sitting down, he is indeed reciting the blessing before performing the Mitzvah, for the primary part of the Mitzvah is sitting in the Sukkah. It seems that it is therefore preferable to recite the blessing while one is still standing and not after he sits down. This is likewise the opinion of the Rambam who rules that one should recite this blessing before sitting down and before reciting the Hamotzi blessing. He writes that this was indeed the custom of the Sephardic (Spanish) sages.
Nevertheless, others write that it is preferable to recite this blessing only after one has been seated in the Sukkah, for actually sitting in the Sukkah is not the essence of the Mitzvah; rather, the Mitzvah is when one remains in the Sukkah to eat. They therefore write that it is better to recite this blessing after the Hamotzi blessing.
Maran Ha’Shulchan Aruch quotes the opinion of the Rambam who writes that one should recite the blessing before sitting down in the Sukkah. Nevertheless, Maran continues that the prevalent custom is to recite the blessing after one has already been seated and after one has already recited the Hamotzi blessing.
Maran Rabbeinu Ovadia Yosef zt”l quotes the words of Maran HaShulchan Aruch and writes that it is nevertheless preferable to follow the opinion of the Rambam and recite the “Leeshev Ba’Sukkah” blessing while one is still standing and only then to sit down and recite the Hamotzi blessing. Hagaon Ya’abetz in his Sefer Mor Uktziah and Hagaon Harav Chaim Palagi in his Sefer Mo’ed Le’Kol Hai rule likewise.
Thus, halachically speaking, it is preferable to recite the “Leeshev Ba’Sukkah” blessing before sitting down to eat in the Sukkah and afterwards, one should be seated and recite Hamotzi. Those who customarily recite the “Leeshev Ba’Sukkah” blessing after reciting the Hamotzi blessing while already seated have on whom to rely.
When Kiddush is recited (either on Yom Tov or Shabbat), one should recite the Kiddush while standing and then recite the “Leeshev Ba’Sukkah” blessing and be seated. On the first night of the Sukkot holiday when “Shehecheyanu” is recited as well, one should recite the “Leeshev Ba’Sukkah” blessing while standing and then recite the “Shehecheyanu” blessing while seated.
On the second night of Sukkot outside of Israel, one should recite “Shehecheyanu” at the end of the Kiddush and only afterwards recite the “Leeshev Ba’Sukkah” blessing.