The Parsha preceding the holiday of Sukkot this year is Ha’azinu. It is well known from Chazal that when a festival falls during the week, it has a connection to the preceding Parsha. The Tur writes {Orach Chaim, 428): פִּקְדוּ וּפִסְחוּ – First, we read Parshat Tzav and then comes the festival of Pesach; וְלִמְעֻבֶּרֶת סִגְרוּ וּפִסְחוּ – In a leap year, we first read Parshat Metzora and then comes the festival of Pesach; מְ נוּ וְעִצְרוּ – First, we read Parshat Bamidbar, where Bnei Yisrael are counted, and then comes the festival of Shavuot; צוּמוּ וּצְלוּ – First, we fast on Tisha B'Av, and then we read Parshat Va'etchanan, which discusses the Tefillah of Moshe Rabbeinu; קוּמוּ וְתִקְעוּ – First, we read Parshat Nitzavim, from the root meaning "standing," and then the blowing of the shofar. Thus, if Parshat Ha’azinu comes before Sukkot, it indicates there is a hint in the Parsha to the festival of Sukkot.
The Torah states (Devarim 32:10):
He found him in a desert land, in a wasteland of howling wilderness. He encircled him, He cared for him, He guarded him like the pupil of His eye. Like an eagle that stirs up its nest, hovers over its young, spreads its wings, takes them, carries them on its wings.
Rashi comments: He surrounded them and encircled them with clouds, and He surrounded them with banners on four sides, and He surrounded them at the foot of the mountain, which He held over them like a barrel – שׁ ֶכָּפָהוּ עֲלֵיהֶם כְּגִיגִית.
The well-known words of the (Sukkah 11b) discuss the disagreement between Rabbi Akiva and Rabbi Eliezer regarding the meaning of the Pasuk:
So that your generations may know that I made Bnei Yisrael dwell in booths when I brought them out of Egypt.
The Gemara states: It was taught, according to Rabbi Eliezer, that these booths were the clouds of glory – the Ananei HaKavod. However, Rabbi Akiva says they made actual booths to shelter themselves. If so, according to Rabbi Eliezer's view, our sitting in the Sukkah is a remembrance of the Ananei HaKavod, and in Parshat Ha’azinu, the Torah deals with the matter of the clouds of glory, as Rashi explains.
Before sitting in the Sukkah, we recite the text:
I am ready and prepared to fulfill the mitzvah of dwelling in the sukkah as the Creator commanded me: "You shall dwell in booths for seven days; all native-born in Israel shall dwell in booths, so that your generations may know that I made the children of Israel dwell in booths when I brought them out of Egypt."
This provides evidence for Rabbi Akiva's opinion, that Hakadosh Baruch Hu caused us to dwell in actual booths.
