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The majority hold that it is forbidden to sleep for even a moment outside the sukkah. It is considered to be foolish to sleep in the sukkah if it's raining. However, all the sources I've found word this halakha along the lines of "if it begins to rain, then he should go inside". They don't seem to contemplate sleeping inside from the outset if it is forecasted to rain. Further, he is permitted to remain sleeping inside after the rain stops. So hypothetically, if one reasonably believed it would rain that night, may he sleep inside from the outset even though he would theoretically be comfortable in the sukkah at the time he goes to sleep if he is reasonably certain it will rain?

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    "The majority hold that it is forbidden to sleep for even a moment outside the sukkah." Majority? Who disagrees with this? It's an explicit Gemara and the unanimous position of all Rishonim. – Double AA Oct 21 '16 at 4:13
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    @DoubleAA there are chassidim who have a minhag not to sleep in the sukkah. I'm not sure how they justify it. – ShamanSTK Oct 21 '16 at 4:14
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    ShamanSTK Those Chasidim have just invented things to be scared of so they become exempt due to Mitztaeir. They don't disagree with the basic rule that you must sleep in the Sukkah any time you can. – Double AA Oct 21 '16 at 4:21
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    @DoubleAA if I had a choice between leaving my house and probably waking up soaked at 2AM, I would leave – Heshy Oct 21 '16 at 14:40
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    @Heshy That's not generally how it works. Have you been woken up by rain in a Sukkah? You don't wake up soaked. Some drops fall on your face and you get up and go inside. It's not much more annoying than having to get up to go to the bathroom in the middle of the night. I don't usually see people sleeping with catheters to avoid that happening... – Double AA Oct 21 '16 at 14:42
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The Ritva' (Sukah 29a, s.v. ת"ר היה אוכל) says if one senses rain and a developing overcast ("shamayim miskadrim b'avim") you're patur from Sukah, under the same exemption as when it is actually raining -"mitztaer". This opinion was later relied upon by the Bikure Yaacov (639:30).

The question contemporary Poskim deal with is if this concept applies to weather reports; that is, if meteorologists forecast rain which is not yet detectable in the sky, and it affects you setting yourself up in the Sukah for some time, like a long meal or going to sleep. So, the halachic jury is still out on this one.....

  • @oliver "was later relied upon" that's a bit of an exaggeration. The Bikure Yaacov only says that if it's cloudy you shouldn't say a blessing on sitting in the Sukkah because Safek Berakhot LeHakel. He doesn't rely on the Ritva to exempt you from going to the Sukkah at all. – Double AA Oct 9 '17 at 5:15
  • @DoubleAA I understand the BY to be relying on Ritva's opinion, i.e. by citing it to bolster his opinion not to say ל״ב when it began drizzling (I understand the third-to-last word "בזה" to refer to his initial scenario). I feel if he disagreed with the Ritva he would have elaborated (if not here then elsewhere). Maybe I'm wrong. – Oliver Oct 9 '17 at 5:34
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Weather forecast are not always accurate and even when the predicted rain does come it may be delayed or possibly not fall in all the predicted locations equally. However if one believes in the accuracy of weather forecasts to the point that the predicted possibility of rain causes him discomfort and anxiety, he is exempt from sleeping in the suka.

http://baisdovyosef.com/faq/630-sleeping-in-the-rain-2/

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