(לט) אַךְ בַּחֲמִשָּׁה עָשָׂר יוֹם לַחֹדֶשׁ הַשְּׁבִיעִי בְּאָסְפְּכֶם אֶת תְּבוּאַת הָאָרֶץ תָּחֹגּוּ אֶת חַג ה' שִׁבְעַת יָמִים בַּיּוֹם הָרִאשׁוֹן שַׁבָּתוֹן וּבַיּוֹם הַשְּׁמִינִי שַׁבָּתוֹן. (מ) וּלְקַחְתֶּם לָכֶם בַּיּוֹם הָרִאשׁוֹן פְּרִי עֵץ הָדָר כַּפֹּת תְּמָרִים וַעֲנַף עֵץ עָבֹת וְעַרְבֵי נָחַל וּשְׂמַחְתֶּם לִפְנֵי ה' אֱלֹקֵיכֶם שִׁבְעַת יָמִים. (מא) וְחַגֹּתֶם אֹתוֹ חַג לַה' שִׁבְעַת יָמִים בַּשָּׁנָה חֻקַּת עוֹלָם לְדֹרֹתֵיכֶם בַּחֹדֶשׁ הַשְּׁבִיעִי תָּחֹגּוּ אֹתוֹ. (מב) בַּסֻּכֹּת תֵּשְׁבוּ שִׁבְעַת יָמִים כָּל הָאֶזְרָח בְּיִשְׂרָאֵל יֵשְׁבוּ בַּסֻּכֹּת. (מג) לְמַעַן יֵדְעוּ דֹרֹתֵיכֶם כִּי בַסֻּכּוֹת הוֹשַׁבְתִּי אֶת בְּנֵי יִשְׂרָאֵל בְּהוֹצִיאִי אוֹתָם מֵאֶרֶץ מִצְרָיִם אֲנִי ה' אֱלֹקֵיכֶם.
39 “‘So beginning with the 15th day of the 7th month, after you have gathered the crops of the land, celebrate the festival to God for seven days; the first day is a day of rest, and the eighth day also is a day of rest. 40 On the first day you are to take branches from abundant, vigorous trees—from palms, willows and other leafy trees—and rejoice before Adonai your God for seven days. 41 Celebrate this as a festival to God for seven days each year. This is to be a lasting ordinance for the generations to come; celebrate it in the seventh month. 42 Live in temporary shelters for seven days: All native-born Israelites are to live in such shelters 43 so your descendants will know that I had the Israelites live in temporary shelters when I brought them out of Egypt. I am the Lord your God.’”
The Gemara asks: This works out well according to the one who said that the sukkot mentioned in the verse: “I made the children of Israel to reside in sukkot” (Leviticus 23:43), were clouds of glory, as it is reasonable that the roofing of the sukka is modeled after clouds. However, according to the one who said that the children of Israel established for themselves actual sukkot in the desert, and the sukkot of today commemorate those, what can be said? According to that opinion, there is no connection between a sukka and a cloud. As it is taught in a baraita that the verse states: “I made the children of Israel to reside in sukkot”; these booths were clouds of glory, this is the statement of Rabbi Eliezer. Rabbi Akiva says: They established for themselves actual sukkot. This works out well according to Rabbi Eliezer; however, according to Rabbi Akiva what can be said?
Rashbam on Leviticus 23:43
“In order that your generations will know that I caused The Children of Israel to dwell in sukkot when I brought them out of Egypt” – This should be interpreted simply, in accordance with those who maintain in Massekhet Sukka (11b) – a literal sukkah... And therefore we come out of homes full of all sorts of goodness at the time of the ingathering and dwell in sukkot, to remember that The Children of Israel had no inheritance in the wilderness and no houses to inhabit. And it was for this reason that the Holy Blessed One established the Festival of Sukkot at the time of the ingathering of grain and wine, “Lest your heart grow haughty over your houses full of all sorts of goodness;” “Lest you say, ‘Our hand has performed this valor for us.’”
One whose head and the greater part of his body were within the sukkah and his table within the house: Bet Shammai say: it is invalid and Bet Hillel say it valid. Bet Hillel said to Bet Shammai: Did it not in fact happen that the elders of Bet Shammai and the elders of Bet Hillel went to visit Rabbi Yohanan ben HaHoroni and found him sitting with his head and the greater part of his body within the sukkah and his table within the house, and they didn’t say anything to him? Bet Shammai said to them: From there [you bring] proof? Indeed they said to him, “If this is your custom, then you have never in your whole life fulfilled the commandment of the sukkah.
Rabbi Alan Lew, z''l, from This is Real and You are Completely Unprepared
...We sit flush with the world, in a ‘house’ that calls attention to the fact that it gives us no shelter. It is not really a house. It is the interrupted idea of a house, a parody of a house…So it is that the sukkah, with its broken lines, its open roof, its walls that don’t quite surround us, calls the idea of the house to mind more forcefully than a house itself might do. And it exposes the idea of a house as an illusion. The idea of a house is that it gives us security, shelter, haven from the storm. But no house can really offer us this. No building of wood and stone can ever afford us protection from the disorder that is always lurking all around us. No shell we put between us an the world can ever really keep us secure from it. And we know this. We never really believed this illusion. That’s why we never felt truly secure in it [...] In the sukkah, a house that is open to the world, a house that freely acknowledges that it cannot be the basis of our security, we let go of this need. The illusion of protection falls away, and suddenly we are flush with our life, feeling our life, following our life, doing its dance, one step after another.
This is a commandment we fulfill not with a gesture or a word, but with our entire body. We sit in the sukkah with our entire body. Only our entire body is capable of knowing what it felt like to leave the burden of Egyptian oppression behind, to let go of it. Egypt in Hebrew is Mitzraim. The root of this word is tzar, a narrowness. Egypt was the narrow place. Only the entire body can know what it felt like to be pushed from a place of dire constriction and into a wilderness, a spacious, open world. Only the body can know what it felt like to be born. Only the body can know the fullness of joy, and this is a commandment that can only be fulfilled with joy.
ליקוטי מוהר״ן קמא מ״ח
וְזֶה בְּחִינַת בִּינָה, שֶׁשָּׁם נוֹצָר הַוָּלָד... וְהִיא בְּחִינַת סֻכָּה, כְּמוֹ שֶׁכָּתוּב: "תְּסֻכֵּנִי בְּבֶטֶן אִמִּי..."
Likutei Moharan Kama 48
(Reb Nahman of Breslov 1772-1810)
And this is the characteristic of bina, from which the fetus is created... and it is the characteristic of the Sukkah, as it says, "Protect me in my mother's womb..."
רש"י ויקרא פרק כג
(לו) עצרת הוא - עצרתי אתכם אצלי כמלך שזימן את בניו לסעודה לכך וכך ימים, כיון שהגיע זמנן להפטר אמר בני בבקשה מכם, עכבו עמי עוד יום אחד, קשה עלי פרידתכם:
Rashi on Vayikra Ch. 23
Atzeret Hu: It is a day of pausing - I have kept you with me, like a king who invited his children for a feast for a certain number of days, when the time came for them to leave, he said: "My children, I beg of you, remain with me one more day; your leaving is difficult for me."