Sukkos as the Shechinah dwelling among us

איתא במד' צרור המור דודי אעפ"י שמיצר ומימר לי בין שדי ילין.

It is brought in the Midrash on "My beloved is to me a bundle of myrrh (tzeror hamor)" — even though He brings me distress (meitzar) and bitterness (meimar), "He shall lie between my breasts" (Shir HaShirim 1:13).

The Midrash plays on "hamor" as "distress and bitterness": even when Klal Yisrael endures the constriction and bitterness of galus, Hashem still rests close to them, "between the breasts."

וכמו שהי' תכלית גלות מצרים שישכון ביניהם כמ"ש אשר הוצאתי אותם כו' לשכני בתוכם.

And just as the purpose of the galus of Mitzrayim was that He would dwell among them, as it says: "whom I brought out… that I may dwell in their midst" (Shemos 29:46).

The entire goal of the exile and redemption of Mitzrayim was so that the Shechinah would rest among Bnei Yisrael — the constriction of galus was a path toward Divine indwelling.

כמו כן בימים הנוראים שנכנסין למשפט ומתענים ביוהכ"פ כדי לבוא לטהרה שיזכו אל השראת השכינה.

So too on the Yamim Nora'im (Days of Awe), when we enter into judgment and afflict ourselves on Yom Kippur in order to arrive at purity, so that we may merit the resting of the Shechinah.

The "distress and bitterness" of the Days of Awe and the fasting of Yom Kippur serve the same purpose as the galus of Mitzrayim: they bring us to taharah, which prepares us for the indwelling of the Shechinah.

וסוכות בחי' בין שדי ילין.

And Sukkos is the aspect of "He shall lie between my breasts."

After the constriction of the Yamim Nora'im comes Sukkos — the time of intimate closeness, when Hashem "lies between the breasts" of Klal Yisrael.

ורומז שני שדיך למשה ואהרן.

And "your two breasts" alludes to Moshe and Aharon.

Chazal interpret the "two breasts" of Shir HaShirim as Moshe and Aharon, the twin sources of nourishment for Bnei Yisrael.

כמו כן סוכה רומז לאהרן ולולב למשה רע"ה.

Likewise the sukkah alludes to Aharon, and the lulav to Moshe Rabbeinu.

The two great mitzvos of Sukkos parallel the "two breasts": the sukkah corresponds to Aharon (the Ananei HaKavod that surrounded us in his merit), and the lulav to Moshe.

כמ"ש במ"א ויקח משה עצמות יוסף עמו.

As I have written elsewhere on "And Moshe took the bones of Yosef with him."

The Sefas Emes refers to his earlier teaching connecting Moshe with Yosef — the lulav, which corresponds to the spinal column and to the tzaddik (Yosef/Moshe), the "spine" of Klal Yisrael.

ולכן כ' למען ידעו כו' בסוכות הושבתי בהוציאי אותם.

And therefore it is written: "so that [your generations] may know that I caused Bnei Yisrael to dwell in sukkos when I brought them out [of Mitzrayim]" (Vayikra 23:43).

The mitzvah of sukkah is explicitly tied to the Exodus, linking the closeness of Sukkos back to the purpose of leaving Mitzrayim.

לידע כי תכלית יציאת מצרים הי' לשכון בתוכם:

To know that the purpose of the Exodus from Mitzrayim was for Him to dwell in their midst.

Dwelling in the sukkah teaches the very lesson of Yetzias Mitzrayim: the whole aim of the redemption was that Hashem should dwell among Bnei Yisrael — the closeness now realized on Sukkos.

Summary: Even amid the "distress and bitterness" of galus and the Yamim Nora'im, Hashem remains close — "He shall lie between my breasts" — because that very constriction, like the galus of Mitzrayim, serves to bring Bnei Yisrael to taharah and to the indwelling of the Shechinah. Sukkos is the realization of that intimacy: the sukkah corresponding to Aharon and the lulav to Moshe (the "two breasts"), and the mitzvah of dwelling in the sukkah teaches that the whole purpose of Yetzias Mitzrayim was for Hashem to dwell among His people.