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Shouldn't the obligation to sit in the Sukkah also fall into the category of Sefeika D'yoma? If so why do some not eat in the Sukkah on Shemini Atzeres?

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Yes, we should. The gemara is Sukkah says this explicitly, and the Rishonim and Shulchan Aruch poskin this way. –  S-B Oct 5 '12 at 17:11
    
@S-B You are certainly right about the explicit gemara, rov rishonim, and shulchan aruch (although some sources would be nice), but that doesn't mean that this is the practice in all communities. This question was looking for the reasons behind those communities who practice otherwise, not judging which way is better. –  Double AA Oct 5 '12 at 18:12
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3 Answers 3

The simple answer would be that we avoid any behavior that slaps the new yomtov of Shmini Atzeres in the face (such as shaking lulav). To eat in the sukkah is no big deal, as plenty of people eat on porches or gazebos or what-have-you when the weather's nice, no religious ritual required. So in places where it was ridiculously cold on Shmini Atzeres, they didn't!

There are Hassidic thinkers who have answers that give the practice more significance (often based on Hassidic or kabbalistic thought), but that would be the simplest answer.

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Shalom, you answered why some do. Read the question. The Q was why some DON'T! –  d a Oct 6 '10 at 0:11
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d a, note the last sentence in Shalom's first paragraph. –  Isaac Moses Oct 6 '10 at 1:16
    
got ya! Thanks!!! –  d a Oct 6 '10 at 3:31
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Rav Tzadok HaCohen of Lublin wrote an over 60 page pamphlet defending the practice of not eating in the Sukkah on Shmini Atzeres, called "Meishiv Tzedek".

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Note the second paragraph of my answer. –  Shalom Oct 6 '10 at 1:38
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His pamphlet is from an Halachic perspective. –  Yahu Oct 6 '10 at 5:41
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Though I believe R' Tzadok is considered a Hassidic thinker. –  Shalom Oct 6 '10 at 14:16
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Shalom, true but since the Kohen has a more famous reputation for Kabbalistic and Hasidic thought, I wanted to let the readers know that this pamphlet is strictly halachic. –  Yahu Oct 11 '10 at 7:11
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Your answer can be improved by summarizing some of the key points in the pamphlet –  Charles Koppelman Oct 5 '12 at 17:34
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see here for an excellent article on topic: [make sure to read the footnotes].

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