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If Lubavitch is careful not to eat or drink anything outside of the sukka, why does Lubavitch not sleep in the Sukka?

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Kopusters do not sleep as well. –  YDK Oct 6 '11 at 2:58
    
Did the Lubavitcher Rebbe ever say that he personally did not sleep in the sukkah? Or just that the custom among the prior Rebbeim was thus? –  Curiouser Mar 2 '12 at 1:37
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@Curiouser: it seems to have varied among the Rebbeim themselves. The expression "how can one sleep in the sukkah" is from the Mittler Rebbe (the second rebbe in the line), but on the other hand we have a report of the Tzemach Tzedek (his successor) telling his attendant to sleep there. As for the last Rebbe, I don't know whether he ever publicly discussed his own practice, but it is known that indeed he didn't sleep there. –  Alex Mar 2 '12 at 4:32
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@ Alex: Thanks; but how would his practice be known? Did someone observe him actually asleep at home? Could he not have slept in the sukkah when he was alone in it? –  Curiouser Mar 2 '12 at 14:54
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I do not have a source for this, but I have heard that Belz's also doesnt sleep in the sukkah.

The reason why Lubavitch does not sleep in the sukkah is explained by the Rebbe in Likkutei Sichos Vol. 29 p. 211

It is very simple to summarize. There is a halacha that if you are uncomfortable in the sukkah you can leave. When it rains most people don't eat in the sukkah but Lubavitch especially the Rebbe was seen many a pouring rain drenched in the sukkah. How then could we not sleep in it? Well it was bitterly cold in Russia. That is not the answer either. The answer is as follows.

The Sukkah al pi kabbalah represents the Makif D'Binah, loosely translated as a transcendent encompassing level of Understanding of Hashem. If you have any perception of this, it is a quite overwhelming level of G-dliness in the Sukkah. It is possible to eat and learn Torah in the Sukkah, but sleep? Impossible. The Chabad Rebbeim literally could not sleep there. [Some say that the Rebbe did not sleep the entire festival of Sukkos, and was therefore able to fulfill both the Halacha and Kabbalah of Sleeping in the Sukkah, or at least did not go to sleep, but rather would just learn until he fell asleep]. What about us? We don't perceive the Makif D'Binah and we wouldn't make it 7 days without sleeping. The answer is that we have such a level of Hiskashrus to our Rebbe that we are pained that he is pained as well as pained that we can't perceive this level of G-dliness. .

On a personal note, I left Lubavitch some years ago and slept in the Sukkah and always was disturbed by something, ie: a dog barking all night, air mattress going flat, and finally the Sukkos before I made my way back to Lubavitch roots I was viciously bitten by insects to the point that I had at least 50 bites on my body.

That was my Makif D'Binah.

The sources for all of this is found in the Sicha quoted above. If you agree or not, this issue was analyzed by the Rebbe with a microscope and if you actually learn the Sicha it is hard to say he is wrong in what he says regardless if you choose to sleep in the sukkah or not.

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Shulchan Aruch, Orach Chaim, Chapter 639, does not include "I'm sad about not being as holy as my rebbe" as a valid reason for ignoring a mitzvas aseh d'oraisa. –  user1095 Mar 2 '12 at 17:25
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As stated below which is why i wont elaborate, the Rogatchover and the Baal HaTanya both rule that sleeping is not an essential part of the mitzvah. Psychological distress is just as valid as physical distress. Please source your opinions. The following sources support my stance. Mishna, Sukkah 20b Code of Jewish Law 639 Code of Jewish Law 640:4 Mordechai Sukkah 741 Rabbeinu Manoach Commentary to Rambam 3:6 6. Levush 640:4 7. Ramo 639:2 8. Taz 639:9 –  user1292 Mar 2 '12 at 19:24
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The Taz is referring to oseik b'mitzvah potur min hamitzvah -- which has nothing to do with psychological distress from a mitzvah. Neither does the Ramo on which he is commenting. The Levush makes my point precisely, in that he only lists physical and not psychological tzar. (His l'mud zchus for not sleeping inside has to do with tircha, which is physical) Nor do the other sources list psychological tzar. Listing a bunch of sources that are irrelevant doesn't really help your case. Just provide one source that allows for being psychologically distressed by the mitzvah as being a p'tur. –  Curiouser Mar 2 '12 at 21:26
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The Baal Hatanya in Shulchan Aruch Harav 639 says to sleep in the sukkah. –  sam Sep 23 '12 at 2:58
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@Curiouser The Rama (OC 640:4) mentions fear of bandits attacking you in the Sukkah as a reason to be exempt due to mitztair. –  Double AA Apr 8 '13 at 2:57
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The reason Chabad Chasidim do not sleep in the Succah is Kabalistic. The enclosed links explains it.

http://hebrewbooks.org/pdfpager.aspx?req=30466&pgnum=245

through

http://hebrewbooks.org/pdfpager.aspx?req=30466&pgnum=255

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those links are to the shaar blat –  Shmuel Brin Oct 4 '11 at 22:53
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Please include at least a brief summary –  yydl Oct 4 '11 at 23:15
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@yydl, it's too long for me to summarize comfortably, but briefly: (a) according to the Rogatchover and the Baal Hatanya, sleeping in the sukkah is not essential to the complete fulfillment of the mitzvah, unlike eating and drinking there; (b) the Chabad rebbeim found it difficult to sleep in the sukkah because of its tremendous holiness; (c) we chassidim follow our rebbeim, and indeed would experience distress if we couldn't do so. –  Alex Oct 5 '11 at 1:43
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@Alex Thank you. –  yydl Oct 5 '11 at 1:44
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The Rebbe actually addressed this question in a letter dated 7 Cheshvan, 5715 [1954]:

Re Sleeping in the Succah In order to safeguard and inspire a greater feeling toward the Succah, sleeping in it is not practiced by us. The basis for this is two-fold: First, we have a rule that Hamitztaer putter min HaSuccah (suffering exempts one from dwelling in the Succah). Secondly, during sleep a person is not in control of himself, and, furthermore, the very act of undressing and dressing, etc. inevitably creates a common-place attitude towards the place which serves as a bedroom. Such a depreciation of attitude toward the Succah (by sleeping in it, as explained above), from what his attitude should properly be towards the Mitzvoth of G-d whereby He has sanctified all Jews, would be deeply felt by the Chabad Chassid by virtue of his Chassidic teachings and upbringing, and would cause him profound spiritual suffering. The combination of these two considerations, therefore, led to the custom not to sleep in the Succah. However, if a Jew feels absolutely certain that his sleeping in the Succah will not in the slightest affect his attitude toward the sanctity of the Succah, and is consequently free from any mental pain that might be caused thereby, he is duty-bound to sleep in it, in accordance with the fullest meaning of Taishvu K'ain taduru, to make his Succah his dwelling place to the utmost.

(Excerpt of letter taken from L'chaim # 688 )

BTW, @mochin rehavim wrote:

I do not have a source for this, but I have heard that Belz's also doesnt sleep in the sukkah.

The Rebbe mentioned this 10 Sivan 5750 – During distribution of dollars for Tzedoka- (the whole conversation can be found in Toras Menachem 5750 Vol 4, P. 325) - where R' Zvi Kahana asked the Rebbe this very question.

PS: To anyone that knows about / read / watched the above 'dollars' encounter and was wondering what was the Rebbe's 'nekudah', well, I saw a blog post about this and one commenter by the name of guravitzer summed it up very well:

Chasidim and Misnagdim disagreed over many things. In the first 2 generations or more, they believed each other to be minim and apikorsim - Misnagdim for not having Yiras Shomayim, Chasidim for not following Shulchan Aruch. In the eyes of Lubavitch, that ended in the time of the Tzemach Tzedek, where as we put it Chasidim discovered that Misnagdim are yere shomayim as well, and Misnagdim discovered that Chasidim follow Shulchan Aruch. They ceased to consider each other a threat, or kofrim, and focused on the Maskilim and the various governments oppressing them. THAT DOES NOT MEAN THEY AGREED WITH EACH OTHER IN MATTER OF HALACHAH OR HASHKAFAH. But the fact that they would work together means they considered each other to be ehrliche Yidden, with reasonable heterim for their behaviors. There was no peace with the Maskilim or the Tzionim for these leaders, as they were truly kofrim.

Thus: The Volozhiners still disagreed with the Rebbeim on all the issued that exist between Chassidim and the other parties. However, they ceased to be opponents. If they felt that not sleeping in the sukkah, or any other issue that the Mirrer RY could have brought up, were reason to lump Lubavitch with the Maskilim, or even to not consider them Frume leaders, they would have said so. Jewish debate was vociferous then - have you read the manifestos about Tzionus?

Nowadays, this is one of the questions used an excuse to be opponents once more. The Rebbe was not asking for all Misnagdim to become Chasidim and agree with all of our Minhogim. The Rebbe wondered why the opposition was revived, which had died out previously, and pointed out one of the weapons used. If the Volozhiners had wanted to be opponents, that could have pulled this out of their arsenal as well.

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Slight error in that blog post: Chassidim never considered misnagdim to be "minim and apikorsim." –  HodofHod Sep 19 '12 at 23:18
    
@HodofHod Good point, you're right. –  Danield Sep 20 '12 at 6:32
    
I just finished reading the comments there, and OY! We need Moshiach. :( –  HodofHod Sep 20 '12 at 17:17
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actually, for that very reason I didn't include a link to the blog post! –  Danield Sep 20 '12 at 20:23
    
I don't understand the Rebbe's wonderment (as expressed by the random commentor). When enemies find common ground against a common enemy, that doesn't mean they start liking each other. Why should anyone be surprised if the original arguments resurface after some initial other threat passes? It's completely obvious that someone who is mavatel aseh deorayta of sleeping in the sukkah is not as bad as one who is kofer betorah min hashamayim. To think that working with Chassidim to fight Maskilim implies a given Shittah of the Chassidim is even an acceptable hava amina is nonsense. –  Double AA Nov 18 '13 at 23:41
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