The work Derech Eretz, which documents the customs of the ancient Jewish community of Halab (Aleppo, Syria), discusses the procedure for the recitation of Kiddush and the Berachot of "Lesheb Ba’sukka" and "She’hehiyanu." As noted in the Mahzorim, on the first night we recite "Le’sheb Ba’sukka" immediately after Kiddush, and then "She’hehiyanu." (On the second night of Sukkot, however, the Beracha of "She’hehiyanu" relates only to the holiday itself, and not to the Misva of Sukka, and so it is recited immediately after the Kiddush, before "Le’sheb Ba’sukka.") Interestingly, on the first night of Sukkot, the Jews of Halab would sit after the Beracha of "Lesheb Ba’sukka" before reciting "She’hehiyanu." This ruling is mentioned by Hacham Yishak Zafrani and Hacham Yaakob Attieh, among other authorities. Nowadays, however, the prevalent practice among Syrian Jews is to remain standing for the Beracha of "She’hehiyanu," and to sit only for the drinking.
On Sukkot morning, the custom is to sit for the recitation of Kiddush and for the Beracha of "Lesheb Ba’sukka." The Beracha of "Lesheb Ba’sukka" goes after the Beracha of Hagefen. One might have assumed that since Berachot over Misvot are always recited before the Misva act, we must remain standing while reciting the Beracha of "Lesheb Ba’sukka," as this Beracha speaks of "sitting" ("Lesheb") in the Sukka. In truth, however, this is incorrect. The term "Lesheb" in this Beracha refers not to sitting, but rather to our being or residing in the Sukka. Thus, for example, if a person does not have a seat in the Sukka and eats standing, he nevertheless recites the Beracha. Hence, we sit when reciting this Beracha on Sukkot morning.
This applies only with regard to a meal with bread that one eats in the Sukka. If, however, one attends a Kiddush in the synagogue’s Sukka, and he will be eating only "Mezonot" food or "She’hakol" food, as opposed to bread, he does not recite the Beracha of "Lesheb Ba’sukka."
Different opinions existed among the Rabbis of Aleppo as to whether on the weekdays of Sukkot, when one eats bread without Kiddush, he recites "Ha’mosi" before "Lesheb Ba’sukka" or after "Lesheb Ba’sukka." Hacham Moshe Tawil, who served as Chief Rabbi of Halab, recited the Beracha of "Ha’mosi" before "Lesheb Ba’sukka," whereas Hacham Abraham Hamoui, in Bet Menuha, writes that the Jews of Halab recited "Lesheb Ba’sukka" before "Ha’mosi," following the ruling of the Ben Ish Hai. Both practices are documented and equally valid.
Summary: On the first night of Sukkot, we recite Kiddush followed by the Beracha of "Lesheb Ba’sukka" and "She’hehiyanu," and we then sit and drink. On the second night, we recite the Beracha of "She’hehiyanu" before "Lesheb Ba’sukka." On Sukkot morning, we sit for Kiddush and then recite "Lesheb Ba’sukka" before drinking. If one eats bread on the weekdays of Sukkot, he must recite the Beracha of "Lesheb Ba’sukka." Some authorities ruled that the Beracha is recited before "Ha’mosi," while others maintain that it should be recited after "Ha’mosi," and both practices are valid.
