The order of the brachot of kidush on Sucot is a halachic issue that functions as a crossroads for several broader halachic discussions. The first question is should the bracha over the wine come first or should the bracha sanctifying the day take precedence. This question is not specific to kidush on Sucot but applies whenever kidush is recited. This issue is found as a dispute between Beit Shamai and Beit Hillel in parallel Mishnayot found in Berachot (51a) and Pesachim (114a). In both Mishnayot the Gemara explains the logic of Beit Shamai. The use of wine is due to the sanctity of the day and therefore its bracha should follow Birkat Kidush (the Bracha sanctifying the day). Secondly, since the sanctity of the day begins with nightfall, which proceeds the meal, the brachot of kidush should reflect that order. On the other hand Beit Hillel is of the opinion that since the wine is a necessity for saying the bracha of kidush it should take precedence. Additionally, since we have a rule that a bracha that is more common proceeds those that are less common the bracha on wine should be said first. On this issue the Gemara states that the halachic ruling follows the opinion of Beit Hillel.
Following the brachot for the wine and the sanctity of the day, we learn in Shulchan Aruch (OC 643), that a bracha for the mitzvah of sitting in the sucah is said. A Birkat Shehecheyanu then follows this bracha. The brachot of kidush proceed those of Sucah and Shehechyanu since the sanctity of the day is a pre-requisite for the mitzvah of sucah.
As for the order of the latter two brachot, the Gemara in Sucah (56b) presents a dispute between Rav and Raba Bar Bar Chana. Rav is of the opinion that a bracha pertaining to the mitzvah of the day should receive priority. Raba Bar Bar Chana is of the opinion that Shehecheyanu should be recited first on the basis of the halachic principle that the more common bracha should receive priority. The Gemarah accepts the opinion of Rav. In the commentaries an additional reason is offered. Since Birkat Shehecheyanu applies to those brachot that proceed it, were it to be said before the bracha for mitzvat sucah, we would relate the Shehechyanu only to the sanctity of sucot and not to the mitzvah of sucah.
This point in turn raises a new debate. When reciting kidush on the second night in the Diaspora should the order of kidush of the first night be maintained or should the order be: Wine, Kedushat Hayom, Shehecheyanu and then Sucah. The issue is based on the accepted opinion that the two days of Yom Tov in the Diaspora are viewed as two separate days each requiring an independent Birkat Shehecheyanu. Yet, the mitzvah of sitting in the sucah is an on going mitzvah and the Shehecheyanu said on the first day applies to Sucot in its entirety. Therefore, the Shehechyanu recited in kidush of the second day applies only to the sanctity of the day and not to the mitzvah of sitting in a sucah. Both the Shulchan Aruch and Rama (OC 661) accept the opinion of the Rosh that the bracha of Shehecheyanu should be said after Birkat kidush, proceeding the bracha for mitzvat Sucah. The rational for the Rosh’s ruling is that since the Shehecheyanu relates only to the kidush, saying Birkat Sucah between kidush and Shehecheyanu would constitute a hefsek (undesired separation). Yet, many of the later poskim
(halachic authorities) quote the opinion of the Ravya who feels that the order of brachot should not be changed. As for the hefsek, their opinion is that any bracha said in the framework of the accepted order of brachot does not constitute a separation.
The bracha of Shehecheyanu itself is a point for halachic discussion. The Gemara in Sucah (46a) quotes a Berayta that states “When one completes constructing his Sucah he recites the Beracha of Shehacheyanu”. According to this ruling the Birkat Shehecheyanu should be said upon completing the construction of the Sucah not when first making use of it. Over the years the custom that developed was not to say the bracha at the time of construction but to do as the Gemara tells us was the custom of Rav Kehana to make the bracha when first fulfilling the mitzvah of Sucah. This custom in turn raises a new question. If Shehecheyanu was said when the sucah was built should it be recited again during the kidush on the first night of Sucot. Certain Rishonim feel that being the bracha of Shehecheyanu for the sucah relates to a sucah for the purpose of Mitzvat Sucah and since the mitzvah applies only at the time there is a kedusha of Yom Tov, the bracha applies to the sanctity of the day as well. Others are of the opinion that a shehecheyanu can not be said on something that has not yet occurred. Therefore at the onset of Yom Tov one would need to recite the Shehecheyanu for the commencement of the Yom Tov. The Achronim debate the issue and conclude that since this would constitute a halachic dilemma no bracha should be said.
A final question pertains to whether the kidush on sucot night should be said standing or sitting. This question is independent of the general question of how kidush all year should be said. Even assuming that all year one is to recite kidush sitting, on sucot the Rambam is of the opinion kidush should be recited standing. The basis for the Rambam’s opinion is that when one sits he has fulfilled the mitzvah of sitting in a sucah. Since the halacha is that a bracha for a mitzvah should be said “Over Le’asiyatam” proceeding the fulfillment of the mitzvah, one should not sit in the sucah before reciting the bracha Leishev Basucah. Being we have determined that Birkat Kidush proceeds the bracha of the sucah, consequently kidush should be recited standing. (See Rambam Sucah 6/12)
The Ravad and other Rishonim disagree with the Rambam on two points. First, contrary to the Rambam they feel that the main expression of the mitzvah is when sitting and eating and only then would one make a bracha. (The Rambam is of the opinion that any time one goes into the sucah even not for the purpose of eating a bracha should be recited.) Secondly, even if one were to accept the view of the Rambam to recite a bracha when not eating, according to many poskim any time the mitzvah has not been completed we may recite the bracha as it is still considered “Over le’asiyatam”. Therefore, since one will be drinking wine and eating in the sucah after reciting the kidush there would be no problem sitting during kidush.
As we have seen kidush on sucot night poses many halachic problems and gives us a window to many halchic issues pertaining to the mitzvah of sitting in a sucah.