Sukkah Observance and Rain: When it comes to sleeping in the sukkah, there are differences in conduct. Although it may appear to conflict with a clear ruling in the Shulchan Aruch of sleeping in the Sukkah, there are other instances where practices deviate from what is explicitly stated. For example, consider the placement of the Chanukah menorah. The Shulchan Aruch dictates that it should be placed outside the door to the street, but in practice, many people place it indoors.
Sukkah and Rainy Days: Sitting in the Sukkah while it rains can be somewhat perplexing. On the first night, it's an absolute requirement, but what about the rest of Sukkot? Interestingly, the students of the Baal Shem Tov used to sit in the Sukkah even when it rained. Rain during Sukkot might appear as a negative sign, as if Hashem doesn't want us to fulfill this mitzvah.
Perspectives on Rainy Sukkot Days: Here are a couple of perspectives:
Other Opportunities: One way to interpret this is that during the daytime, there are plenty of opportunities to be in the Sukkah, suggesting that Hashem does desire our service. Rather than leaving the Sukkah in frustration, one should exit humbly, recognizing that the opportunity to serve Hashem remains.
Leaving vs. Not Entering: There's a distinction between leaving the Sukkah due to rain and never entering it in the first place. Leaving when it rains may carry a greater sense of rejection than not entering at all.
Adapting to Circumstances: It's worth considering that relocating a gathering or event indoors due to rain can also be interpreted as a sign that Hashem wants us to be comfortable. This allows us to celebrate or engage in meaningful activities in a more comfortable environment, similar to studying and praying in a synagogue instead of the Sukkah.
Leishev Basukah when it rains and Ushpizin in Chabad: Regarding the recitation of the blessing 'Leishev basukah' when it rains, some individuals may object to it. Traditional Jewish texts do contain strong language regarding those who sit in the Sukkah when it is not required.
However, in Chabad tradition, it is noted in an anecdotal account from the Rebbe's diary that on the second night of Sukkot when it was pouring rain, the Rebbe's father-in-law, the previous Rebbe, did recite the 'Leishev basukah' blessing. This suggests that in Chabad, the practice is to recite this blessing even in the face of inclement weather.
Chasidic Ushpizin Tradition: In Chabad, the practice of inviting the Ushpizin (spiritual guests) during the festival of Sukkot involves a unique approach. While Chabad Chasidim may not recite the traditional Aramaic invitation formula, as is common in some other Jewish traditions, they still engage with the concept and study about it.
Chasidic Ushpizin Figures: Chabad tradition adds an extra layer to the Ushpizin by introducing the concept of the Chasidic Ushpizin. These Chasidic Ushpizin are figures from Chabad Chasidic history and leadership, beginning with the Baal Shem Tov (the founder of Chasidism), the Magid of Mezritch (his disciple), and the Alter Rebbe (the first Rebbe of Chabad).
Teaching from Ushpizin: The Rebbe would often speak about the Ushpizin during Sukkot, deriving meaningful lessons and teachings from the specific Ushpizin associated with each day of the holiday.