If we follow the chronological order of events as they occured in the Torah, then the following question can be asked. Why is Sukkos celebrated now directly after Yom Kippur instead of after Pesach? It was specifically immediately after leaving Mitzrayim that the Torah tells us that Bnei Yisroel camped in a place called Sukkot, where we were so physically vulnerable yet we had total Emunah in Hashem that everything will be ok. Furthermore, we know the Sukkah’s we build on Sukkos are to remind us of the Ananei Hakavod, the clouds of glory. These miraculous clouds that appeared and surrounded Bnai Yisroel, served to protect them immediately after leaving Mitzrayim. So again, it would only make sense that soon after Pesach, the holiday that commemorates leaving Mitzrayim, that we would be given the Mitzvah to celebrate Sukkos. Why is it that at a time that is already so saturated with holidays such as Rosh Hashanah, Yom Kippur and Simchas Torah, that we are given the Mitzvah to celebrate Sukkos?
The answer has to do with the somewhat strange yet special relationship we have with Hashem at this time of the year. We just completed Rosh Hashanah where we affirmed our commitment to Hashem as we proclaimed him as our King and established ourselves as his loyal nation. But within almost no time at all we stand on Yom Kippur confessing our DIS-loyalty to him. Brazenly, with an attempt to use our fresh renewed relationship with our King, we hope to “come clean” and confess the many times throughout the year that we placed our own priorities over his commandments. Now if we were to attempt this with a king of flesh and blood, certainly the confession of disloyalty would greatly subtract from the relationship we so recently sought to rekindle. It would evoke a cloud of doubt in the king that perhap it was all just a selfish act. Maybe we showered him with praise on his inauguration day only to win favor in his eyes, knowing that soon we will need to confess our wrongdoings and desperately need his compassion or else be faced with severe consequences. But when we are dealing with the King of all Kings, our Father in heaven, then the outcome is very different. Instead - Hashem gives us Sukkos!
Sukkos is the response Hashem gives us because he knows that not so deep down we truly truly love him and want to be as loyal to him as we can. It would be quite normal for a person, that after confessing all his horrible wrongdoings to someone, to want to run and hide under a rock to avoid the harsh rebuke and deserved punishment coming his way. Therefore, Hashem lovingly brings us closer to him now more than ever. He tells us that there is absolutely nothing to fear and that his love for us is totally unconditional. So much so, that he tells us that we should leave our secure homes and come outside so that he himself can protect us directly just like he did for us immediately after leaving Mitzrayim when he gave us the Ananei Hakavod. It’s as if to say, that just because we filled an entire day going through the long list of things we did deliberately against His Will, still our relationship with our loving King is not scarred in any way whatsoever. In fact it’s so ironclad, just like the day we left mitzrayim, that there is nothing at all separating us apart. The Sukkah is Hashem’s way of sheltering us directly with His embrace, the same way a parent tightly hugs their child lovingly to reassure them that everything will be just fine. Hashem knows that after a sincere Yom Kippur there is nothing more important to his children now than to know that their Father loves them more than anything in the world and nothing can change that.