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Beit Midrash
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In the midrash (Sifra, Emor 12) we find three explanations for this mitzva. There is an opinion that the sukka is to be made from the four species which are waved on Sukkot, which implies that it is essentially part of one unit with the mitzva of the four species. It is difficult, though, to divorce the mitzva from the historical context to which the p’sukim refer explicitly.
Rabbi Eliezer says that it commemorates the actual booths in which Bnei Yisrael lived in the desert after leaving Egypt. We relive the experience by going into similar booths. One difficulty with this is that the holiday should, then, ostensibly have been in Nisan, when Bnei Yisrael started to occupy such sukkot. (Many answers have been given for this question.)
Rabbi Akiva says that the sukkot in which Bnei Yisrael lived after leaving Egypt were divine clouds. These clouds also began upon leaving Egypt (see Shemot 13:20-23), and so the same question of why they are commemorated in Tishrei is pertinent. We will suggest an explanation within the opinion of Rabbi Akiva, which will also answer this question.
After the sin of the Golden Calf and the resulting great spiritual fall, the question of the relationship between Hashem and Bnei Yisrael came to the fore. Was the "proposal of marriage" and "joint life under one roof" still intact, as it had been before the sin? The answer to this question was given 80 days after the sin. After Moshe’s third stint of 40 days on Sinai, he was able to inform Bnei Yisrael that Hashem had forgiven them. Then Hashem invited Moshe to stand on a rock, while Hashem covered him with "His hand" until He passed (Shemot 33:21-22). The word for covering is "sakkoti," which is etymologically closely related to "sukka." Similarly, David spoke about being hidden in Hashem’s sukka on a bad day and being uplifted at a rock (Tehillim 27:5). When Moshe entered that sukka of sorts, it symbolized forgiveness and a return to His graces and the reappearance of the divine clouds.
All of this happened on Yom Kippur. Therefore, it is appropriate that we celebrate the return to the special historical sukka at the time of year that they returned, right after Yom Kippur. This is one more way in which Sukkot is a continuation of the days of mercy and forgiveness of Yom Kippur.
Let us pray that we will merit hearing the tiding "I have forgiven" and return to find a safe place in the shade of the Divine Presence. This is the deep significance of the cloud that the sukka represents according to Rabbi Akiva.
Rabbis in Midrash
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Kuzari -Rabbi Ari Shvat Kuzari class 9 - "Seeing is Believing" (parag. 21-30)
These paragraphs elaborate on the theme that seeing and knowing is better than any attempt to prove logically, and begins explaining the difference between Israel and gentiles.
Ein Aya Various Universal Stages of the Geula Process
Rav Kook examines the various stages of redemption, explaining how (in addition to the obvious oft-mentioned stages of ingathering the exiles, reviving the Hebrew language, army, state etc.) the messianic dream of world prosperity, the State of Israel and world unity can and are realistically and logically gradually coming true.
Kuzari -Rabbi Ari Shvat Kuzari class 8- "Answering Questions on the Kuzari's Proof from Mass Revelation
How do we know that the "claim" of mass revelation to 2,000,000 witnesses at Mt. Sinai is really true? This important class answers all of the questions skeptics ask about this claim of the Kuzari.
Ein Aya Armies Still Necessary for Balance & the War Against Wars
Rav Kook explains why the world was originally divided into the various seemingly contradicting ideologies and cultures, in order to develop each one respectively. Swords or armies symbolize how each respective ideology defends themselves, as well as deters their opposing ideologies and cultures. On the other hand, the messianic era will be one of peace, and Rav Kook explains the transition to that stage, which mankind is already undergoing.
The Land of Israel LGBT'S IN ISRAEL
The question was asked, how can one make Aliyah with the LGBT parades?
Kuzari -Rabbi Ari Shvat Kuzari class 7 - Five Accumulative Proofs of G-d
As a preparation for the Kuzari's classic proof of G-d from the mass-revelation at Sinai, we start here with 5 other directions to strengthen our belief which also contribute to what the Kuzari will present as well.
Ein Aya Muscle & Meaning: The Dual Nature of Gevurah (Physical Strength)
Is physical strength and fitness a necessity or an ideal? Although it if often totally overlooked among topics of Judaism, Rav Kook writes that it clearly is also a necessity to deter the many enemies of Israel, but even in Y'mot HaMashiach, in the Messianic era, to a certain extent, it's ideal continues even after our enemies will have been finished off.
