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Eating and sleeping in the Sukkah
- Outside Israel, on the eighth day of Sukkot (first day of Shemini Aseret), one should eat in the Sukkah without a Bracha of Leshev BaSukkah. There’s a minhag to be lenient regarding eating in the Sukkah on Shemini Aseret, however, one should not follow this unless one has accepted this practice from his parents or rabbis. 
- Regarding sleeping in the Sukkah on the eighth day of Sukkot (Shemini Aseret), there’s a dispute in the achronim. The Ashkenazim minhag is not to sleep in the Sukkah, while Sephardim hold that one must sleep in the Sukkah. 
An American in Israel
- A Jew from outside Israel who is visiting Israel for Sukkot should not eat in the Sukkah if it’s difficult to sit alone in the Sukkah.  However, if he is alone anyway, such as if he’s in a hotel, Sephardim holds that he should eat in the Sukkah, while Ashkenazim hold that in Israel one doesn't sit in the Sukkah on Shemini Aseret. 
- In Israel one does not eat or sleep in the Sukkah on Shemini Aseret (as it is no longer Sukkot). 
- In Israel, if one must eat or sleep in a Sukkah on Shemini Aseret as there’s no room inside, then one should remove 4x4 tefachim of S'chach to show that one doesn’t intend to add to the mitzvah (Baal Tosif). 
- An alternative to removing S'chach is to put a tarp on top or below 4x4 Tefachim of S'chach as long as the tarp is within 3 Tefachim of the S'chach. 
- It’s permissible to eat in the Sukkah after Shemini Aseret and it’s not an issue of Bal Tosif. 
- It’s permissible to eat or sleep in the Sukkah before Sukkot (erev Sukkot) and it’s not an issue of Bal Tosif. 
- Many poskim say that one shouldn't start the meal until it is certainly nightfall (i.e. Tzet HaKochavim). However, after the fact, if one did start the meal before one should not make the bracha of Leshev BaSukkah if one is eating in the Sukkah. 
- Similarly, one should not make Kiddush on the night of Simchat Torah before certain nightfall (i.e. Tzet HaCochavim). 
- On Shemini Aseret outside Israel the Torah reading is Kol Bechor in Parshat Reah. If Shemini Aseret falls out on Shabbat, the torah reading begins from Asar Taaser. 
- Rambam (Sukkah 6:13), Tur and S”A 668:1 write that one should eat in the Sukkah on the eighth day of Sukkot but not make a Bracha (based on Gemara Sukkot 47a). Kitzur S"A 138:4 agrees.
- There’s an old minhag to be lenient not to eat in the Sukkah on Shemini Aseret from the time of Rashi recorded in Sefer HaPardes, Machzor Vitri (Siman 284), and Maharil (Hilchot lulav) (see Natai Gavreil (Arba Minim) Sh”t 4). The Piskei Teshuvot 668:1 brings in the name of the achronim that there’s room to be lenient since the Korban Netanel writes that the entire establishment of sitting in the Sukkah on the eighth day is based on the assumption that it’s comfortable and beloved to a person, however, if it’s cold or wind is present then one shouldn’t sit in the Sukkah. However, the Piskei Teshuvot concludes that one must be stringent based on the Sh”t Divrei Israel 1:200 that one shouldn't follow this minhag unless one has a tradition for it and it’s not comfortable outside. Aruch HaShulchan 668:3 writes that the gedolim have criticized those who just eat Kiddish in the Sukkah and then eat a meal inside. Mishna Brurah 668:5 also seems to hold that regarding eating one shouldn’t change from the ruling of S”A (which is based on an explicit gemara). Chazon Ovadyah (Sukkot pg 479) also rules like Shulchan Aruch.
- Darkei Moshe 668:2 writes that there’s room to be lenient regarding sleeping outside the Sukkah. Kitzur S"A 138:5 writes that while the minhag is to be lenient about sleeping in the sukkah, it's proper to be strict. Mishna Brurah 668:6 brings the opinion of the Gra who holds that one must sleep in the Sukkah on the eighth day but concludes that the minhag is to be lenient not to sleep in the Sukkah. However, the Bet Yosef 668 writes that sleeping is no different than eating in the Sukkah. Therefore, Chazon Ovadyah Sukkot (pg 479) rules that Sephardim must sleep in the Sukkah like any other night of Sukkot.
- Natai Gavriel (Hilchot Arbah Minim Sh”t 8), Sh”t Minchat Yitzchak 9:54, Rabbi Shlomo Zalman Auerbach in Sh”t Minchat Shlomo 1:19, Rabbi Ovadyah Yosef in Chazon Ovadyah Sukkot (pg 480-1), Ot Hei LeOlam (vol 2 pg 87c; quoted by Sdei Chemed Sukkah 1)
- Chazon Ovadyah Sukkot (pg 480-1) writes explicitly that if it’s not difficult to eat in the Sukkah such as one is staying by himself then he should sit in the Sukkah. However, Sh”t Minchat Shlomo 1:19 exempts such a person in all circumstances. So writes the Piskei Teshuvot 668:2 in name of Sh”t Minchat Yitzchak and Sh”t Minchat Shlomo.
- S"A 666:1, Natai Gavriel (Sukkot 81:4)
- S”A 666:1 writes that in Israel, if one must eat or sleep in a Sukkah on Shemini Aseret as there’s no room inside, then one should remove 4x4 tefachim of S'chach to show that one doesn’t intend to add to the mitzvah (Baal Tosif). Mishna Brurah 666:5 explains that there’s no real Bal Tosif since one doesn’t violate Bal Tosif unless one intends to add to the mitzvah while it isn't the time of the mitzvah, however, there is an issue of appearing like adding to the mitzvah which is only applicable on Shemini Aseret. Natai Gavriel 81:4 writes simply that same needs to be done if one needs to sleep in the Sukkah on Shemini Aseret.
- Piskei Teshuvot Piskei Teshuvot 666:1 quotes the Bikurei Yacov 666:5 who says that using 4x4 invalid S'chach isn't sufficient against the Bigdei Yesha who permits but then adds that even the Bikurei Yacov agrees that putting a tarp 4x4 tefachim on top or below the shach within 3 tefachim of the S'chach is sufficient.
- Rama 666:1 writes that it’s clear that one isn’t sitting in the Sukkah to fulfill the mitzvah after Sukkot and so there’s no issue of Bal Tosif, however it would be an issue on Shemini Aseret because it’s so close to the holiday.
- Chazon Ovadyah pg 481 holds that’s there no issue of Bal Tosif before the mitzvah was done. Interestingly, Piskei Teshuvot 666:1 raises this issue (writes that it’s strange that no one addresses this issue) and concludes leniently and adds that it’s preferable to eat a meal or snack (KeBaytzah of mezonot) outside the Sukkah after eating in the Sukkah to show that one clearly doesn’t want to add to the mitzvah.
- Magan Avraham 668:3 quotes the Maharshal who writes that one shouldn't make Kiddish on Shemini Aseret until it is nightfall so as not to enter into a situation where there is a doubt if one will be able to make the bracha of Leshev BeSukkah. Many achronim including the Levush 668:1, Chaye Adam 153:5, Kitzur S"A 138:4, Aruch HaShulchan 668:6, Kaf HaChaim 668:10, Mishna Brurah 668:7, Nitai Gavriel 85:4, and Chazon Ovadyah (p. 669) agree. Chazon Ovadyah writes that there is even more reason for this law in Israel. [The term that the Magen Avraham uses, "Ad SheTechshach" in context clearly means certain nighttime which is after Tzet HaKochavim. This term is also used in the Mishna (pesachim 99b) and there the Mishna Brurah 472:5 explains it to mean Tzet HaCochavim.]
- Kaf HaChaim 668:10 quoting Ben Ish Chai (Vezot HaBrachot #13), Nitai Gavriel 92:2
- The gemara Megillah 31a writes that the torah reading for Shemini Aseret is Kol Bechor. S"A 668:1 codifies this halacha. Kaf HaChaim 668:17 explains that we read Kol Bechor because it includes a hidden reference to Shemini Aseret in the words VeHayita Ach Samech which chazal explain to mean that Shemini Aseret is included in the Simcha of Sukkot.