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The Rokeach § 219 (brought by Eliyah Rabbah 625:1) brings those who say that when Rabbi Akiva (Sukkah 11b) says that Sukkos commemorates the sukkos that the Jews dwelled in, it's referring to when they fought against Sichon and Og (Numbers 21:21-35).

Eliyah Rabbah (basically the same as what the Rokeach himself writes):

והרוקח הלכות סוכה סי' ריט כתכ כשצלו על ארץ סיחון ועוג ועל כרכים שבארץ כנען אז ישבו בסוכות, וזה 'למען ידעו וכו''‏

It sounds like the time that they lived in sukkos was specifically while fighting Sichon and Og (or at least it started at that time).

Why would this be? In general I would ask why would they be in sukkos if they had the Clouds of Glory protecting them (which everyone agrees with, just Rabbi Akiva says that's not what the holiday of Sukkos commemorates). But assuming they were dwelling in sukkos, why was it only during this time period?

My only guess is when Aharon died, the clouds dissipated (inter alia Rosh Hashanah 3a (brought by Rashi to Numbers 21:1), Taanis 9a). That's when they needed to build shelters. Ta'anis says that the Clouds of Glory returned in the merit of Moshe. It doesn't say when. Perhaps it was after they fought Sichon and Og (which happened seemingly soon after Aharon died (Numbers 20:22-29).

Does anyone explain this Rokeach?

  • "But assuming they were dwelling in sukkos, why was it only during this time period?" I don't see from your paraphrase that it was only at that time. Maybe they were in booths other times, too, but only the ones from that time are commemorated. – msh210 Oct 13 at 7:35
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The Chasam Sofer in his Torah commentary and Responsa (O.C. 185) explains that the army left the camp in order to wage war and was thus no longer surrounded by the Clouds of Glory. The Sukkah commemorates entering the land of Israel, which commenced with these battles fought by soldiers who needed the shelter of physical booths. See the commentary for a further explanation of how the two opinions in the Gemarah are actually closely related to each other based on this understanding.

It seems to me that the Chasam Sofer's explanation is indicated by the Rokeach himself who quotes the verse from Shmuel 2 11:11:

וַיֹּ֨אמֶר אוּרִיָּ֜ה אֶל־דָּוִ֗ד הָ֠אָרוֹן וְיִשְׂרָאֵ֨ל וִֽיהוּדָ֜ה יֹשְׁבִ֣ים בַּסֻּכּ֗וֹת

and explains that they would use booths for shelter in the fields until the war was won.

  • 3
    Where is this chasam Sofer? – robev Oct 13 at 13:51
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    What about the wars with Midyan and Amalek? – DonielF Oct 13 at 15:20
  • @DonielF I was going to ask that as well. Although, the war with Amalek didn't seem to go for so long, but I could be wrong – robev Oct 13 at 18:25
  • @DonielF See the edited answer – Jay Oct 13 at 18:30
  • @robev I've added a link to one source, and I think he writes about it elsewhere as well. – Jay Oct 13 at 18:32

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