By Rabbi Yerachmiel D. Fried

Dear Rabbi,
I have often wondered if there’s a reason that the holidays of Yom Kippur and Sukkot fall so closely together. Is it a coincidence, or is there some connection between the two?
— Lee W.
Dear Lee,
The two holidays are actually intertwined in a deep way. We’ll try to touch on some of the connections.
When sitting in the sukkah, according to one opinion in the Talmud, we celebrate the booths the Jews sat in when leaving Egypt. Another opinion is that we commemorate the miraculous Clouds of Glory, which protected and shaded the Jewish people during the 40 years of travels in the desert.
Those Clouds of Glory actually disappeared when the Jews lost their deep connection through the sin of the golden calf. They were almost destroyed due to this sin, equated to idol worship, so soon after receiving the Ten Commandments at Mount Sinai. Then began a three-month period of prayer and repentance, eventually leading up to the day when God finally uttered to Moses, “I have forgiven as you requested.” This is the day that became known as Yom Kippur, the Day of Atonement.
Although the Jews were forgiven, God’s divine presence, the Shechinah, still remained removed from them. To not have the loving connection they had enjoyed since they left Egypt, feeling God’s tangible presence among them, was a deep source of sorrows to the Jews. Their chance to return the Shechinah to the camp of the Jews was to build the Tabernacle, a kind of movable golden Temple that would travel with them throughout their sojourn in the desert.
The commandment to build the Tabernacle was given to Moses the day after Yom Kippur. The next day, Moses transmitted the commandment. The following two days, the Jews began gathering the necessary materials to construct this edifice, and the day thereafter they began the long, difficult process of building the tabernacle.
That was five days after the first Yom Kippur, the 15th of the month of Tishrei. God, on that day, to show His pleasure that the Jews had fully repented and desired His presence so badly, returned the Clouds of Glory that had been remiss since the golden calf. That was a day of incredible joy and ecstasy among the people, as they saw their repentance was complete, their eternal connection to God irrevocable.
That day, the 15th of Tishrei, is the first day of Sukkot. It is the day of celebration of the Clouds of Glory — not the clouds that accompanied the Jews from the day they left Egypt, but the clouds that returned after their repentance at Yom Kippur.
This is one reason that Sukkot, more than any holiday, is referred to in the prayer book/siddur as “the time of our joy.”
All the Jewish holidays carry with them a mitzvah to be joyous, but Sukkot transcends the others in this way. I’ll illustrate it with an example. Imagine a mother sitting in the waiting room, her eyes filled with tears, not knowing if her son’s risky operation will work, his life holding on barely by a thread. Suddenly, the doctor emerges, “Lady, a miracle’s happened, it worked. Your son’s going to live and be fine.”
Those tears of pain and fear are transformed into tears of joy, her joy and ecstasy going far beyond the joy many could imagine.
The Jews were nearly destroyed because of the golden calf, their existence held on by a thread. Tears of joy finally replaced their tears of repentance when those Clouds of Glory were returned. It was the ultimate celebration of Yom Kippur’s message of mercy and forgiveness, that their eternity is secure.
This remains our joy on Sukkot until today. It is the joy that year after year, generation after generation, God continues to forgive us on Yom Kippur, and despite every attempt to destroy us and all we’ve done wrong throughout our history, the miracle of Jewish survival is still intact, and we’re still here to sit in our booths today.
Rabbi Yerachmiel D. Fried, noted scholar and author of numerous works on Jewish law, philosophy and Talmud, is founder and dean of DATA, the Dallas Kollel. Questions can be sent to him at yfried@sbcglobal.net.