makes his sukkah – which is simple faith – primary. It should be a well-established feature of his life, “and his home” – meaning his intellect, as it says (Mishlei 24:3), “with wisdom a home is built” – secondary.
(Ohr Yisrael by Harav Hakadosh Reb Yisrael of Sadigura, p. 248)
In Fulfilling the Mitzvah of Sukkah, One Shows that He Believes in Hashem
In Yalkut Shimoni on Parshas Emor it is written regarding the passuk, “And the sukkah shall be their shade during the day”: If someone fulfills the mitzvah of sukkah in this world, Hakadosh Baruch Hu protects him from harm.... Why is this the reward specifically for the mitzvah of sukkah? Don’t all mitzvos protect us, like a shield, from evil?
Perhaps this can be understood as follows: Dovid Hamelech said (Tehillim 32:10), “One who trusts in Hashem will be surrounded by chessed.” On the other hand, one who does not truly believe in hashgachah is not protected. As the Torah warns (Vayikra 26:23-24), “...if you shall walk with Me ‘keri,’ I shall walk with you ‘b’keri’ as well....” Rambam explains that keri implies that a person says that things are happenstance, and if so, Hashem in turn will leave that person to happenstance. Sefarim hakedoshim teach that the mitzvah of sitting in the sukkah alludes to the fact that we are trusting in the shade of Hakadosh Baruch Hu, and we believe that Hashem yisbarach is always watching us.
This, then, is the meaning of the Yalkut: “Anyone who does the mitzvah of sukkah in this world” – through which he shows that he believes that everything happens with Hashem yisbarach’s hashgachah – Hashem protects him from harm, and no evil will befall him.
(Kesav Sofer on the Torah, Likutim for Sukkos)
The Mitzvah of Sukkah Comes to Arouse the Middah of Bitachon
The meaning of this is that the mitzvah of sukkah comes to teach us that a person should not place his trust in his home and its strength...even if his home is filled with everything good. He should not trust in the help of any person, even if the person is the ruler of the country; rather, he should place his trust in He Whose words created the world’s reality – for only He has the ability, and when He promises something, He doesn’t rescind His promise.... And we should seek protection from Him alone....
The mitzvah of sukkah comes after the ingathering of the silo and the vineyard in Eretz Yisrael, in order to arouse us to this truth. This time of year [has the potential to be] a time when people neglect emunah. All the storage houses are filled, and the person is in his own home and city, and he has repaired his roof and strengthened his home to protect himself from rain and wind and other possible harm. Therefore, the Torah commands him to leave his strong home and to sit in the sukkah, so that he will be aroused to place his trust in Hashem yisbarach, and he will pay attention to the fact that everything that came from the field – it all came with the will of Hashem.
This is hinted to by the fact that the sukkah is made from the remains of the silo and the winepress. This serves to remind him that he reaped fruit to eat, and the remains are also used [as sechach] for the sukkah, [as we have all this] only because Hashem made it rain; and then he’ll remember that whatever protects him, and all his possessions, come only from Hashem yisbarach and not from his own actions....
(Menoras Hama’or, Ner 3, unit 4, section 6, ch. 1)
Sukkah Alludes to Emunah
“For all seven days, a person makes his sukkah primary and his home secondary” (Sukkah 28a).
“Sukkah” refers to emunah, and it is the canopy of emunah. So long as a person hasn’t fully perfected the “seven middos,” he must follow the path of emunah peshutah, and he cannot follow a path of emunah on the basis of his intellect. That’s why the Mishnah says, “for all seven days,” implying that so long as he is still in the process of perfecting the seven middos and hasn’t yet perfected them all, “a person makes his sukkah” – which is simple faith – primary. It should be a well-established feature of his life, “and his home” – meaning his intellect, as it says (Mishlei 24:3), “with wisdom a home is built” – secondary.
(Ohr Yisrael by Harav Hakadosh Reb Yisrael of Sadigura, p. 248)