1. By keeping the commandment of sukkah, a person is capable of tearing up the evil decree he was sentenced to during the High Holidays. The Yetav Lev brings that even if he was given a verdict on Rosh Hashana and Yom Kippur that he was guilty, he can take the letters of the word “guilty” (chayav) and exchange them with the first letters of the verse “the pious will exult, they will sing with reverence” (Y’alzu CHassidim B’chvod Yerananu). This means that by being happy and exulting with performing the commandment of sukkah, he can actually tear up his guilty verdict.
2. A person is rewarded for making a sukkah by being saved from harsh sentences and punishments. The source for this is the Zohar, which states that Jacob fled from his brother Esau into a sukkah.
3. The Tiferet Shlomo explains our sages’ statement “One who is in discomfort is exempt from living in a sukkah” (מצטער פטור מסוכה) to mean that “The one who is in distress will escape his tribulations in the merit of keeping the commandment of sukkah.” Similarly, the statement “The sick and their attendants are exempt from being in a sukkah” can be interpreted to mean “The sick will escape their sickness and pain in the merit of keeping the commandment of sukkah.”
4. The Sfat Emet explains the blessing in the Shemoneh Esreh “The King Who causes death and restores life and causes deliverance to sprout forth” in this way:
“The King” — this refers to G-d on Rosh Hashana;
“who causes death and restores life” — on Yom Kippur, when our Creator sits on the throne in judgment and apportions life to all His creations;
“and causes deliverance to sprout forth” — on Sukkot, a time auspicious for salvations which can nullify evil decrees.
All the judgments on Rosh Hashana come to bring about this deliverance.
5. One who fulfills the commandment of sukkah will merit long life. This is hinted to in the verse: “Every born Jew shall dwell in a sukkah”. Ezrach (born Jew) is equal in numerology to Gevurah, because G-d promised that all those who dwell in a sukkah will reach old age. A verse in Psalms calls living to the hoary age of 80 Gvurot.
6. The Kaf Ha-Chaim brings in the name of the Yafeh Lalev: “One who is very careful with the commandment of sukkah, and performs it exactly according to law is guaranteed not to have quarrels inside his home that year.” The Segulat Israel brings that the commandment of sukkah is auspicious to save one from controversy: “He should learn the tractate of Sukkah the entire year, as it says, “protect them in a sukkah from the strife of tongues.” (Ps. 31:21)
The Four Species
The Sefer Ha-Chinuch says that an etrog is like a heart which is the dwelling place of the intelligence — to hint that a person shall serve his Creator with all his mind. Thelulav (palm branch) is like a spine which passes through most of a man’s body, to hint that his entire body should be dedicated to G-d’s service. The hadassim (myrtle) leaves are like eyes to hint that one shouldn’t follow the desires of his eyes, and the aravot (willow) leaves are like lips which are the part of the body that enables speech. All four species are taken together to remind him of the war he must wage to subdue his body demands. If he falls, he shouldn’t despair, but should immediately strengthen himself to continue on with his battle.
7. Taking a lulav with an arava is auspicious to have children who will not die young and will be virtuous.
8. Lulav is combined of two numbers 36 (לו) and 32 (לב). The 36 corresponds to the 36 righteous people who live in every generation and the 36 tractates of the Talmud. The 32 corresponds to the Torah which starts with a ב and ends with a ל. Lulav in numerology equals chayim, “life”, i.e. the Torah. The lulav gives a person the merit to have righteous children whose heart will be drawn after the Torah.
9. The Rosh writes in the name of the Yerushalmi that we shake the Four Species during the prayer of Hallel to weaken the power of the Accuser.
The Commandment to Be Happy on the Festival
10. The Peleh Yoetz brings in the name of Gurei Ha’Ari that whoever is happy and good of heart and doesn’t feel any sadness on this holy day, is guaranteed to have a good year and always be happy.
11. The Rambam writes: “The happiness a person should feel on Sukkot is happiness at fulfilling the commandments and loving G-d who commanded them.
12. The Vilna Gaon said that despite this being one of the most difficult commandments to keep on the festival, a person should try “to rejoice and be happy every single second of the festival and not let himself come to sadness even for one second.”
13. One should pray at length and ask G-d to feel happiness in his mind. King David prayed for happiness: “Make the soul of Your servant happy.” We likewise pray in the Shemoneh Esreh: “Remove from us all sorrow and moaning.”