It is a mitzvah to dwell in a sukkah on Sukkos; therefore, we recite the brocha of leishev ba’sukkah when we fulfill the mitzvah. When we dwell in the sukkah, we should have in mind that Hashem commanded us to sit in a sukkah to commemorate how Hashem surrounded us with clouds during Yetzias Mitzrayim.1
The primary way of fulfilling the mitzvah of dwelling in the sukkah is by eating a seudah with bread or mezonos foods2, so the brocha of leishev ba’sukkah is recited along with the brocha on the food. There are
other ways to fulfill the mitzvah of living in a sukkah in the same fashion as one would in their own home, so other activities that are usually done at home are also included in the mitzvah. Some examples are: spending time in the sukkah learning or having a significant drink, like wine.
Where to Build a Sukkah
A kosher sukkah must belong to the owner, or be gifted to him, so when building the sukkah, one should build it on his own property or in an area where he was permitted to build. If the sukkah was built in a public area (like on the sidewalk) without receiving permission to do so, one cannot recite the brocha of leishev ba’sukkah, although the mitzvah of sukkah was fulfilled b’di’eved.3
Using the Same Sukkah Throughout the Day
The brocha of leishev ba’sukkah is specific to the sukkah one is currently using. Once the brocha was recited along with the brocha on food4, the brocha is not recited when relaxing, sleeping, or drinking in the sukkah for the entire day, as all other activities (even past and future ones) are included in the brocha on the meal. Even if one has a second meal, there is no need to make the brocha again if one stayed inside the sukkah or left only for a short period of time (about an hour or two), having in mind to return. If, however, one leaves the sukkah for a long time or without planning to return, they should recite the brocha
of leishev ba’sukkah on another meal (not on a drink or relaxing in the sukkah, as they are still included in the initial brocha from earlier in the day).
Going to a Different Sukkah
If one leaves a sukkah and continues eating in a different sukkah, or even if he goes there just to relax (without eating), according to the basic Halacha, he should recite the brocha of leishev ba’sukkah again.5 It is a common practice to eat a k’beitza of mezonos and make the brocha of leishev ba’sukkah while having in mind to include all other activities in the sukkah, as “relaxing” is not clearly defined.
There is a disagreement regarding the requirement to recite the brocha of leishev ba’sukkah on significant drinks.6 This is also why some do not say the brocha of leishev ba’sukkah during Havdalah, although the
prevalent custom is to say the brocha.7
If One Forgot to Say the Brocha
If one forgot to say leishev ba’sukkah until after one finished the meal, one may recite the brocha while still sitting in the sukkah, as it is also a part of the mitzvah.8
Kiddush
At the Yom Tov and Shabbos night seudos, the brocha of leishev ba’sukkah is recited on wine directly after Kiddush because the holiday of Sukkos and the mitzvah of sitting in the sukkah are mentioned during Kiddush. On the first night of Sukkos the brocha of leishev ba’sukkah comes before shehechyanu, because we say shehechyanu over both the Yom Tov and over the mitzvah of sukkah. On the second night, we say shehechyanu before leishev
ba’sukkah since shehechyanu is only over the Yom Tov, not the sukkah.9
During the day Kiddush (on Yom Tov and Shabbos), many recite leishev ba’sukkah after Kiddush10, which is the custom of Chabad and others, while some say it after hamotzi. During all other times, it is recited immediately after hamotzi or mezonos11, as the meal is the main part of the mitzvah.12
The prevalent custom is to recite the brocha of leishev ba’sukkah while sitting. However, those who say Kiddush while standing may say it while standing, as both ways are permitted.13
שו’’ע הרב תרכ’’ה ס’’א 1
שם תרל’’ט ס י’’א וי’’ב 2
ג או’’ח תרל‘‘ז ס’ י’’א שם 3
שם 4
שם ס’ י’’ד ט’’ו 5
שם ס’ ט’’ו 6
לוח א’’י, רי’’מ טוקצ’ינסקי 7
שם ס’ ט’’ז 8
שם סי’ תרמ’’ג ס’ א’. וראה בסידור ע’’א 9
10 Sefer HaMinhagim, Reshimus
שם ס’’ד 11
שם ס’’ג 12
שם סי’ תרמ’’ג ס’’ב 13