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If it is raining on the first night of Sukkot, Rema Orach Chayyim 639:5 writes:

לילה הראשונה צריך לאכול כזית בסוכה אף אם גשמים יורדין ויקדש בסוכה כדי שיאמר זמן על הסוכה

On the first night, one must eat a kezayit [of bread] in the sukkah, even if rain is falling. One makes kiddush in the sukkah in order to recite shehecheyanu in the sukkah.

Mishnah Berurah 639:35 quotes opinions that do not allow one to recite the blessing of leisheiv basukkah under such circumstances. He therefore advises one to wait to recite kiddush (for an hour or two, or possibly even until midnight) because:

פן יעבור הגשם דאם יעבור יכנס לסוכה ויברך ברכת לישב בסוכה ויאכל ויוצא בזה המ"ע לכו"ע

Maybe the rain will clear, and if it does, he can then go into the sukkah, make the blessing of leisheiv basukkah and eat and thus fulfill the biblical mitzvah according to all opinions.

I don't understand why one needs to wait to eat. Why can't you make kiddush in the sukkah and simply omit leisheiv? Then eat the entire meal in the house (assuming one can obviate issues with kiddush bimkom seudah). Then wait as long as you can (perhaps until midnight) for the rain to stop, in which case you return to the sukkah, recite leisheiv and eat a kezayit of bread. If the rain doesn't stop, then, before you go to sleep, simply eat a kezayit of bread in the sukkah in the rain, without leisheiv.

The advantage of this method is that this doesn't interfere with one's simchat yom tov (a concern Mishnah Berurah himself worries about in this very same paragraph.)

One issue I can see with this method is that you are reciting shehecheyanu during kiddush on the sukkah at a time when you may be exempt from the mitzvah. However, as Mishnah Berurah points out in his next paragraph:

דאפילו אם נימא דפטור אז מסוכה מ"מ יוצא בזה דלא גריע ד"ז מאלו בירך שהחיינו בחול בשעת עשייה בסוכה דיוצא בזה

Even if we say that one was exempt at that time [when he said shehecheyanu in the sukkah while it was raining on the first night], he has nevertheless fulfilled his obligtion. This is because it is no worse than had he recited shehecheyanu before yom tov when he built the sukkah, in which case one has fulfilled the obligation.

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  • Sorta similar judaism.stackexchange.com/q/76915/759 My feeling has been that since the Gemara mentions how to say Leishev with Kiddush, Rishonim assume there's value to saying them together. I don't know what that value is. – Double AA♦ Aug 19 '18 at 13:31
  • @DoubleAA That's an interesting suggestion to explore. Worth noting in that context is that if it's raining on the second night, MB rules to make kiddush in the house without leisheiv. (Although even there he thinks it's a good idea to wait a bit.) – Joel K Aug 19 '18 at 13:38
  • probably because not everyone always had enough bread; and/or once people eat bread they feel full and might not want to eat again. Second night could be worried about sefeika d'yoma. – David Kenner Aug 19 '18 at 16:38
  • @JoelK It's interesting that MB has different rules for the 2nd night. I wonder what he says to do if it rained both nights. – DanF Aug 20 '18 at 14:09
  • I wonder if he feels there's a Bittul Aseh by actively eating bread outside the Sukkah before having eaten the obligatory bread inside. Consider the case of Pesach night: if you don't have enough Matza you can eat Matza at Afikoman and eat Matza Ashira at the beginning of the meal, but maybe eating real Matza without the Mitzva before doing it for the Mitzva (is that possible?) would be Bittul Aseh. For sukkot the parallel solution, since egg challah is generally seen as acceptable for the first night, might be Pat HaBa BeKisnin? – Double AA♦ May 30 at 16:05
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The peninei Halacha says (my translation):

למנהג אשכנז, העומד לאכול שיעור שחייבים לאוכלו בסוכה, מברך על אכילתו 'לישב בסוכה'. לפיכך, המתכוון לאכול פת או מזונות כשיעור יותר מנפח 'ביצה', יחד עם הברכה על האוכל מברך 'לישב בסוכה'. ומי שאינו מתכוון לאכול כשיעור זה במשך כל שהייתו הנוכחית בסוכה, יברך 'לישב בסוכה' גם על טעימה כל שהיא של מזונות או יין או מאכל חשוב אחר. ואף שיש בזה עוד מנהגים, כך ראוי לנהוג.

According to the ashkenazi custom, one who plans to eat an amount that one must eat in the sukkah (ie kebeitza) blesses “leishev besukkah”. Therefore if one plans to eat more than on kebeitza of bread or mezonos, says leishev besukkah in addition to the blessing on the food. But one who doesn’t plan on eating a kebeitza during this whole time in the sukkah, says “leishev besukkah” on even a small taste (is less than a kebeitza, probably less than a kezayis) of mezonos OR WINE or any other important food. And even though there are other traditions, this is the best way to act.

We see from here that one may not drink wine while in the sukkah without saying leishev besukkah, if he’s not planning to eat bread or mezonos before leaving (which is exactly the given case).
Furthermore, the Mishna Berurah prohibits saying Kiddush in the rain, and gives the reason that it is because of the safek of leishev basukkah, which implies that according to the Mishnah Berurah as well, in this case one must say leishev basukkah even on wine according to some opinions, so the safek stands even for wine.

The same is true in the given case if it continues raining: one may not eat a kezayis of bread in the sukkah without saying leishev besukkah (and one may not say leishev besukkah while it’s raining according to some opinions, as mentioned in the question). Therefore the suggested solution doesn’t work, and we have to wait until the rain clears.

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    1) as noted by the Pninei Halakha not everyone holds of this so the question holds for the other opinions 2) does anyone hold you need a leshev basukkah on wine the first night in the rain? The only possible reason to eat in the rain the first night is the opinion that you must have some bread in the Sukkah like you must have Matza the first night of pesach. Nothing about wine or any other food. Everyone would agree you don't need to drink wine in the rain in the Sukkah ever. – Double AA♦ May 29 at 23:02
  • @DoubleAA but since the Mishna Berurah doesn’t allow saying kiddish in the sukkah in the rain because some hold that he can’t say leishev now, it seems logical that the Mishna Berurah holds that one does need to say leishev on wine (at least in this case). Therefore, it seems that there is a mitzva to drink wine in the sukkah. – Lo ani May 30 at 17:15
  • Well, that's the OPs question. Is that why the MB doesn't allow Kiddush in the rain first? You've asserted that, but I question it. The OP wasn't sure why the MB doesn't allow saying Kiddush right away in the Sukkah and eating inside before returning later. – Double AA♦ May 30 at 17:18
  • (on the other hand, Misvara you'd expect the Brakha in the case of rain the first night to be said not during Kiddush according to the Rama, but he never says that. hmmm) – Double AA♦ May 31 at 21:17
  • @DoubleAA why else would the MB be Machmir, if not because of the problem of leishev? In fact, we can be Medayek from the MB (if the OP quoted and understood him correctly) that he holds that this problem is the reason he is Machmir: “Mishnah Berurah 639:35][2] quotes opinions that do not allow one to recite the blessing of leisheiv basukkah under such circumstances. He THEREFORE advises one to wait to recite kiddush”. Therefore, meaning because of the safek of leishev. – Lo ani Jun 1 at 21:34

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