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In the midrash we find three explanations for this mitzva.

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Sukkot is the climax of agricultural success, but also brings with it the anxiety & nervousness regarding the upcoming season. The Sukkah represents the clouds which precede the rainy season, & are the time when God judges us regarding rain. Cherophobia is a common problem where happiness & accomplishment are accompanied by fear: After I've achieved my goals, there's a feeling of emptiness- What do I do now?!". Also, we ask like Kohelet, "Why am I still not happy?!". There's also the fear that I may lose or someone will take away what I've achieved. Also the fear "what if people reveal that I'm really not so talented?". Sukkot are termed in kabbala: "The Shade of Emuna", that only God has absolute success, & only He can provide security regarding past & future.

Sukkot stories

"Rabbi Alnekaveh told a story he heard once from an etrog-seller who used to bring Rav Eliyahu etrogim to check: "It is well-known that Rab Eliyahu could look at an etrog for mere seconds and immediately discern its advantages and defects..."

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Parashiot Shema Israel and Vehaya im shamoa contain the indispensable principles of the special nature of living in the Land of Israel. Therefore, Moshe teaches the people of Israel these Parashiot at the threshold of The Promised Land.

COMPARE AND CONSIDER

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