Sleeping in Sukkah
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Exemptions from Sleeping in the Sukkah
- If it’s cold outside, many have the practice not to sleep in the Sukkah and some poskim defend this practice. However, many poskim hold that one should make an extra effort to sleep in the Sukkah (either by making a insulated Sukkah, by bringing in heaters, or by toughing it out). 
- A person who is afraid of bandits at night is exempt from sleeping in the Sukkah. Similarly, one is exempt from sleeping in the sukkah if he is genuinely afraid of terrorists in a place where that is relevant. 
- Some Chasidim have the practice of not sleeping in the Sukkah. 
If it Rains
- If it rains one is exempt from sleeping in the sukkah.
- Even after it stops raining one doesn't have to go back into the sukkah even if one wakes up in the middle of the night since that is considered a pain to have to move into the sukkah in the middle of one's sleep. Similarly, if when it was raining in the night a person put up a shlock on top of the sukkah he can sleep in the sukkah with the shlock on top and even if it stops raining he can continue to sleep there since it would be a pain to have to remove it. However, if it is easy to remove the shlock then he should do so. 
- If a person knows that it is going to certainly rain but has not started to rain, some poskim hold that one is exempt at this point since it will be a pain to have to wake up and move one's bed out of the sukkah when it starts to rain, while others hold that he is obligated until it starts to rain.
- A man who has a baby that wakes up in the middle of the night and his wife needs him to take care of the baby is exempt from sleeping in the sukkah.
Sleeping in a small Sukkah
- One is obligated to sleep in a small Sukkah even if that means bending or folding one’s body and there’s no exemption of being uncomfortable in the Sukkah (like there is if it rains). 
Leaving the table in the Sukkah
- Even though one major authority states that one must leave the table in the Sukkah while one sleeps, many disagree and say that one doesn’t need to be strict but should be if there’s no need to remove the table and so is the custom. 
- One may sleep under the table in the Sukkah if it’s not Ten Tefachim high. 
Taking a short nap
- It’s forbidden to sleep outside a Sukkah whether it’s a fixed sleep or a short nap.  (however, it's not even considered a nap if it's less than 53.7 seconds and many poskim hold that it's permissible while some forbid even that).  Additionally, Hacham Ovadia Yosef provides a leniency for anyone who is prone to sickness to take naps outside of the Sukkah. 
- Many married men are lenient not to sleep in the Sukkah because sleeping alone wouldn't be a fulfillment of the mitzvah of living in the sukkah like we live in our homes. It is preferable that a man sleep with his wife in the Sukkah (not on nights of Onah or her Tevilah) to fulfill the requirement of dwelling in the Sukkah like one would in one’s home. However, some poskim hold that one shouldn't be lenient for these reasons. 
- On a night when the couple has Onah or the night of Tevilah the man isn't obligated to sleep in the Sukkah. 
- A married man in the first year of his marriage, some say that he shouldn't sleep in the Sukkah in order to keep his wife company at night while others believe there is no difference for sleeping in the between a man in the first year of marriage or any other time.
Sleeping alone in the Sukkah
- It is permissible to sleep alone in the Sukkah even though one shouldn't sleep alone in a house. 
If one's traveling
- One is allowed to travel by bus for business purposes even if one knows that one will fall asleep on the way and one does not have to stand up so as not to fall asleep outside the Sukkah. However, if one is traveling for a leisure trip one may not sleep outside the Sukkah and one may not even nap on the bus. 
Other activities in the Sukkah
- Rama 639:2 defends the practice of those who are lenient in not sleeping in the Sukkah saying that where it's too cold it's painful to sleep there and so one may sleep outside the Sukkah. Mishna Brurah 639:17 comments that this is so if one doesn't have proper pillows and blankets to keep one warm (implying that if one has proper coats and blankets one should sleep in the Sukkah.)[see Nemukei Orach Chaim 639:1 who discusses this at length.] Chazon Ovadyah pg 195 rules like the Rama. Yalkut Yosef (Sukkah pg 722 and 725)
- Rama 640:4
- Rav Avigdor Neventzal in his Mishnah Brurah Biytizchak Yikare on Rama 639:2
- See Likkutei Sichos, Vol. XXIX, pp. 211-219 quoted by chabad.org
- Shulchan Aruch OC 639:7
- Shulchan Aruch OC 639:7. Mishna Brurah 639:40 quotes a machloket achronim if a person woke up because of the rain and moved inside but before he fell asleep it stopped raining whether he has to return to the sukkah. The Rama 639:7 clarifies that once he is exempt because of the rain he can sleep until he wakes up in the morning and he doesn't have to get someone to wake him up in the morning so that he can sleep in the sukkah.
- Mishna Brurah 639:41
- Shevet Hakehati 1:199 holds that even if one sees that it is cloudy and going to rain as long as it didn't yet rain one is obligated in the sukkah and his proof is from Shulchan Aruch 639:5 and Shaar Hatziyun 639:60. Dirshu 639:40 cites Rav Nissim Karelitz (Chut Shani Sukkot p. 247) as holding that one is exempt and Rav Elyashiv (Ashrei Haish 3:26:30) held that one was obligated until it started to rain.
- Chazon Ovadia (Sukkot p. 200). Shevet Hakehati 1:198 writes that the man who needs to take care of the baby in the night is exempt from the sukkah even before the baby cries because if he sleeps in the sukkah he won't hear the baby. His ruling is based on Shulchan Aruch 640:3 that those who are taking care of the sick are exempt from the sukkah.
- Rama 640:4, Chazon Ovadyah pg 194)
- Mishna Brurah 640:27 writes that if one takes the table out of the Sukkah in order to sleep one doesn’t fulfill the mitzvah since the Sukkah must be useful for all purposes and if one isn’t able to sleep in it with a table, one doesn’t fulfill the mitzvah of eating it in either. At first glance there appear to be no early sources to corroborate this stringency, however Mikrai Kodesh (Siman 35 pg 155) and Sh”t Shraga Meir 5:55 both try to defend the Mishna Brurah. Moadim UZmanim (Rav Moshe Shternbach; Vol 1, Siman 87) quotes someone who actually saw the Chafetz Chaim act this way in practice. Orchot Rabbenu (Vol 2 pg 229) writes that that the practice of the Steipler would leave a small table in his Sukkah when he slept. Similarly, Sh”t Az Nidabru 14:1 writes once such a holy mouth said such a ruling it’s proper to follow it. On the other hand, many achronim including Rabbi Eliezer Waldenburg in Sh”t Tzitz Eliezer 8:33, Rav Ovadyah Yosef in Chazon Ovadyah (pg 198), Rav Moshe Shternbach in Moadim UZmanim (Vol 1, Siman 87), and Piskei Teshuvot 640:8 argue on the Mishna Brurah saying that there’s no source for such a stringency and conclude that one may remove the tables if there’s a need for room to people to sleep (even a child who reached the age of Chinuch). Chazon Ovadyah and Moadim Uzmanim write the minhag is to remove the tables.
- Natai Gavriel 59:19 based on S”A 627:1
- S”A 639:2; Yalkut Yosef, Moadim, laws of dwelling in the Sukkah, 10
- Mishna Brurah 639:11 writes that even though one may not take a short nap outside the Sukkah one may take a nap that's less than the time it takes to walk 100 steps. Mishna Brurah 44:4 defines this time as around 1/67 of an hour (which is 53.7 seconds). Kaf HaChaim 639:27, Pri Megadim (M"Z 639:5), and Natai Gavriel 59:2 (as first stam-anonymous opinion) agree with Mishna Brurah. However, Bikurei Yacov 639:12 and Hilchot Chag BeChag (pg 44) argue on Mishna Brurah and forbid for any amount of time.
- Yalkut Yosef, Moadim, laws of dwelling in the Sukkah, 10
- Rama 639:2 writes that reason for those who don't sleep in the sukkah if a married man would sleep alone in the sukkah that wouldn't be a fulfillment of the concept of dwelling in the sukkah like we dwell in our homes during the year. However, he concludes that it is preferable to sleep in a private sukkah with his wife. The Taz 639:9 asks on the Rama that if he is correct the Sukkah should be pasul since it isn't fit to be used for sleeping (Rama 640:3). Rather he defends the minhag in another fashion. He writes that a married man has a mitzvah to sleep in the same room as his wife to gladden his wife even if she isn't tahor. That mitzvah makes him exempt from the sukkah. The Magen Avraham 639:8 has a different justification which is that a person would be pained about not being able to sleep in the same room as his wife and someone who is pained by the sukkah is exempt. He explains that this doesn't render the sukkah pasul since it is fit for sleeping and he just has a personal external exemption. Rav Ovadia Yosef in Chazon Ovadyah (pg 196) agrees with the Taz.
- The Gra 639:13 argues with the Rama. Following the Gra, Mishna Brurah 639:18 writes that men are obligated to sleep in the Sukkah without their wives and it’s not pained by not sleeping in the same room as his wife unless it’s the night of Onah.
- Rama 639:2 writes that many are lenient not to sleep in the Sukkah since a man can’t sleep with his wife in the Sukkah unless he has a private Sukkah. However, the Mishna Brurah 639:18 quotes the Gra who argues on this saying that a married man is obligated in Sukkah even if he can’t sleep with his wife in the Sukkah. However, the Mishna Brurah concludes that on nights when there is a mitzvah of Oneh or the women has her Tevilah night, they may sleep outside the Sukkah so as not to miss the mitzvah of Pru Urevu, assuming that it’s not private enough in the Sukkah. This is also the opinion of Chazon Ovadyah (pg 194, 82, and 130).
- Chazon Ovadia p. 196 quotes a dispute between the Divrei Yatziv OC 274 who holds that in the first year of marriage a man should keep his wife company at night as he has a mitzvah to gladden his wife and the Shalmei Moed p. 114 who thinks that there's no difference between the first year and any other, but if the wife is scared to sleep alone indoors her husband is exempt from sleeping in the sukkah.
- Maaseh Rav (Siman 214), Nefesh Kol Chai (Samach #4), Yafeh Lelev 2:1, Bikurei Yacov 639:18, Torat HaMoedim (Rabbi Efraim Oved) 6:3
- Torat HaMoedim (Rabbi Efraim Oved) 6:2 and 10:10 based on Shulchan Aruch 640:8. BeYitzchak Yikra 640:8 quotes Rav Shlomo Zalman who holds that a trip isn't considered someone who's traveling that could be exempt from the Sukkah and so one can't nap on the bus. See also Halichot Shlomo 9:21.