Eating in the Sukkah
The berachah of Leisheiv Basukkah is only made on Hamotzi or Mezonos larger than the size of a beitzah (i.e., more than 54 cubic cm.). Both berachos are said before beginning to eat: first Hamotzi or Mezonos, and then Leisheiv Basukkah.
If you forgot to say Leisheiv Basukkah before eating, say it when you remember (during the meal, or even afterward).
If you left the sukkah and returned soon after, do not say Leisheiv Basukkah again. However, if you only returned after an hour or two, say the berachah again (if eating the above amount of Hamotzi or Mezonos). Similarly, say the berachah again if you left the sukkah having in mind to stay outside for an hour or two, even if you then changed your mind and entered the sukkah soon after.
If you entered another sukkah and will eat there the above amount of Mezonos or Hamotzi, say the berachah again. In fact, even entering another sukkah to spend time there necessitates saying the berachah again. If you are unsure if your visit falls into this category, it is recommended to eat the above amount of Mezonos so you will be able to make the berachah without questions.
It is permitted to eat less than the above amount of Hamotzi or Mezonos outside the sukkah, as well as all other foods or drinks. However, those who are mehader refrain even from drinking water outside the sukkah.
On the first night of Sukkos, you must eat at least a kezayis of bread/challah in the sukkah, even if it is raining. During the rest of Sukkos, it is permitted to enter the house if it rains. However, it is our minhag to eat in the sukkah even when it is raining, and to say Leisheiv Basukkah as well. There were times when the Rebbe farbrenged in the sukkah in the rain.
On the first night of Sukkos, make sure to eat in the sukkah after tzeis hakochavim and before chatzos.
Those who follow Minhag Chabad do not sleep in the sukkah.
“How can one sleep in [the sukkah, which is illuminated by] the makifim of binah?!” (The Mitteler Rebbe, cited in Likkutei Sichos vol. 29, p. 211)
Since Chassidim are mekushar to the Rebbeim, learn their torah, and follow their ways, they refrain from sleeping in the sukkah, just as the Rebbeim did. Additionally, deviating from the practice of the Rebbeim causes them pain, and the halachah is that if sleeping in the sukkah will cause you pain, you are exempt from doing so (Likkutei Sichos ibid., p. 218).
Although women are exempt from eating in the sukkah, they may say Leisheiv Basukkah if they choose to eat there.
Boys from the age of six and over (or five, if the child is bright) should be educated to eat in the sukkah. However, a mother may serve her son food indoors, as long as she doesn’t tell him explicitly to eat it outside of the sukkah.
