Eating in the Sukkah
The berachah of Leisheiv Basukkah is only made on Hamotzi or Mezonos larger than the size of a beitzah (56 g/2 oz). First say Hamotzi or Mezonos, and then say Leisheiv Basukkah. If you forgot to say Leisheiv Basukkah before eating, say it when you remember (during the meal, or even afterward).
It is permitted to consume less than the above amount of Hamotzi or Mezonos outside the sukkah, as well as all other foods and drinks. However, those who are mehader refrain even from drinking water outside the sukkah.
If you left the sukkah for a lengthy period of time (an hour or two), or if you had in mind to leave for a lengthy period of time (even if you then changed your mind and returned soon after), say Leisheiv Basukkah again (if eating the above amount of Hamotzi or Mezonos). However, if you had in mind to return soon after and indeed did so, do not say Leisheiv Basukkah again.
If you entered another sukkah and will eat there the above amount of Mezonos or Hamotzi, say the berachah again. This is true even if the second sukkah is next to the first, and even if you will not need to make a new birchas hanehenin (for example, if you had in mind when making Hamotzi to switch to the other sukkah during the meal). 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 or Hamotzi so you will be able to make the berachah without questions.
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 teachings 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.
Shaking the Lulav
A left-handed person should hold the lulav in his left hand and the esrog in his right hand. When giving your arba minim to someone else to use for the mitzvah, it is advised to tell him/her clearly that it is a present on condition that he/she return them (matanah al menas lehachzir), especially on the first day of Sukkos. However, the other person fulfills the mitzvah even if you did not say so. On the first two days of Sukkos, do not give your arba minim to a child to use as a present until all the adults have used them.
