The Torah tells us to dwell in a hut (sukkah) for seven days. And it gives a reason why: “So that coming generations shall know that I caused the children of Israel to dwell in sukkot when I took them out of the land of Egypt.”1

So what were these exodus-facilitating sukkot that we eternalize by sitting in huts?

Rabbi Eliezer explains: They were the miraculous Clouds of Glory that surrounded us on all sides and protected us throughout our 40-year sojourn in the wilderness.23

And how do you go about dwelling in a sukkah? Well, the oral tradition is that you live in a temporary hut built for shade in the same way you live in your home.4 What’s one of the main things you do in your home? Why, eating meals, of course! So one of the main mitzvahs on the holiday of Sukkot is to eat in a sukkah.

Okay, but we need some details, because otherwise everyone is going to take that very differently. We need to know who needs to eat what and when. And what if it’s raining, or smelly, or otherwise really uncomfortable out there?

Hang in there.

Why Are You Here?

Like the verse said, you’re sitting in this sukkah to re-experience a pivotal memory that sits deep within the consciousness of the nation. So it’s not just where you sit—it’s also what you think. That’s a key part of the mitzvah.

So when you enter the sukkah, you need to remind yourself that you’re doing this to fulfill G‑d’s commandment to dwell in a sukkah to commemorate the Exodus from Egypt.5

There’s also a blessing for dwelling in a sukkah. But you only say it when you’re sitting down to eat something that must be eaten in a sukkah (we’ll get to that eventually). Say it after you say your blessing on the food, before you eat it:

Boruch Atah… leshev ba-sukkah (Blessed are You, L‑rd our G‑d, King of the universe, who has sanctified us with His commandments, and commanded us to dwell in the sukkah).

Who Sits in the Sukkah?

Adults: Men over the age of bar mitzvah (13) are obligatory sukkah-dwellers. Women are non-obligatory sukkah-dwellers.6 Ashkenazic women generally recite the blessing leshev ba-sukkah just as the men do,7 while Sephardic women generally do not.8 (There are some Sephardic communities in which the women do recite a blessing.9)

Children: Technically, the kids should be exempt, as they are from all mitzvahs. But the ancient sages insist that we educate and train them to do mitzvahs. So once a boy reaches an age when he no longer needs the constant attention of his mother (usually 5-6 years old), he should be sitting there with the men.10

There are certain situations that might exempt some people from this mitzvah; for example, if someone is sick. See What About People Who Are Ill? below.

What Do I Eat in There?

Well, what do you eat at home? Most people generally have their main meals at home, but snack outside of the house.

So that’s how it works: If you’re eating a full meal, eat it in the sukkah, and say the sukkah blessing. If it’s a snack, you can eat it there as well, and that is indeed the custom of many, including Chabad. But you technically don’t have to, so don’t say the sukkah blessing.11

What’s considered a snack? If it’s not made of grain, it’s a snack. If it’s grain-based food that is equal to or less than an egg-sized portion (54 cc/grams), it’s also a snack. Bigger than that and it’s a meal.12

Basically, you could have a complete meal with non-grain foods, and you still wouldn’t be required to eat those foods inside a sukkah.13

But, hey, we love mitzvahs. We chase them down and grab them at any opportunity. It’s a privilege and a joy to eat in a sukkah. So despite the above, many, including Chabad, have the custom to not even drink water outside the sukkah.

Drinks: A casual drink, even of wine, is OK outside the sukkah. But let’s say you’re sitting down with friends to enjoy some wine or a few beers, you need to do it in the sukkah. However, if it’s not with a meal, don’t recite the sukkah blessing.14

Kiddush: The exception to this rule is kiddush (and havdalah—see next point). Then the ceremony lends drinking special weight. So, before drinking it, you need to say the leshev ba-sukkah blessing.15

Havdalah: Havdalah should be made in the sukkah, just as it is usually done in the home all year.16

According to many,17 including Chabad,18 you would also recite the sukkah blessing. (Many opine that this would only apply if the havdalah was made over actual wine.19)

(There are some who have doubts whether you really can say the sukkah blessing with just havdalah.20 They suggest eating some grain-based food in the sukkah right after havdalah.21 This is not the Chabad custom.)

Of course, as mentioned above, many, including Chabad, have the custom of not eating or drinking anything, including water, outside of the sukkah.

When Do We Sit in the Sukkah?

On the first night of Sukkot, some time between nightfall and midnight, we all have to eat a minimum amount of bread in the sukkah.22 It’s similar to the requirement to eat matzah on the night of Passover before midnight.

However, during the other days of Sukkot, you can technically choose to only eat foods that aren’t required to be eaten in the sukkah.23

Of course, there is still the mitzvah of having Shabbat and holiday meals with bread, so you would have to eat the bread in the sukkah.24

What If It Rains (Other Than The First Night)?

If it were raining inside your house, would you sit there? Or would you go to your brother-in-law or a restaurant instead?

Same with your sukkah—since you’re treating it like your home. If it’s uncomfortable, you leave. If enough rain is falling to mess up a dish of uncooked beans, you can eat in your year-round home instead (even if you have no beans). If you don’t know how much rain it takes to mess up beans (like most of us), just figure: If you were sitting in your house and this were happening, would you stick it out, or get out?25

Do you say the sukkah blessing if eating in the rain? That’s a whole discussion. Ask the rabbi of your community for his opinion.

The Chabad custom is to eat in the sukkah regardless of the weather. How could you be uncomfortable sitting inside a mitzvah?

The rules for the first night of Sukkot, however, are different.

What About the First Night?

You have to eat at least a kezayit (olive-sized portion) of bread (ideally an egg-sized portion) in the sukkah on the first night of Sukkot. So make sure to make kiddush, and at the very least eat a kezayit of bread in the sukkah after nightfall but before halachic midnight of the first night.26

Ashkenazic custom (including Chabad): If it’s raining on the first night, even if you would ordinarily not eat in the sukkah when it rains, you would still make kiddush and eat at least a kezayit (ideally an egg-sized portion) of bread with the sukkah blessing.27

Other Ashkenazim wait an hour or two to see whether the rain will stop, and if it does, they eat in the sukkah with the sukkah blessing. If the rain persists, they recite kiddush and eat a kezayit of bread in the sukkah without the sukkah blessing.28

Sephardic custom: If it rains on the first night of Sukkot, you are exempt from the sukkah and can eat in your house.29 You also have the option to wait briefly for the rain to subside, as long as it doesn't lead to discomfort on Yom Tov. If the rain ceases before halachic midnight, go into the sukkah, recite the sukkah blessing, and eat a kezayit of bread. However, if it's after midnight, the sukkah blessing is only recited if you eat a kebeitza (egg-sized portion) of bread.30

Do I Make Another Blessing if I Leave and Return?

If there's been an interval or interruption between your current meal and the previous one, then you need to recite a new blessing. If not, then you don't repeat the blessing since the prior one still applies.31

If you leave the sukkah after eating and don’t intend to return within one to two32 hours, then, even if you do return immediately, you need to recite the blessing again before eating. Similarly, if you intended to return within one to two hours but actually came back sooner, it's considered an interval, and you recite the blessing before eating a kebeitza of grain-based food.33

If you stay in the sukkah throughout all seven days of Sukkot without any breaks, then you would only recite the blessing once.34

What About Going From One Sukkah to Another?

In every sukkah in which you eat the requisite amount, the blessing is recited. This applies even if you planned to eat in the second sukkah when making the blessing in the first. Even if the sukkahs are adjacent to each other and you would not be required to make a new first blessing on the food, you would still need to say a new sukkah blessing.35

What About People Who Are Ill?

If you aren’t well, you should try (if it won’t be detrimental to your health) to eat the minimum amount (a kezayit) inside the sukkah on the first night.36 You have no obligation to eat in the sukkah for the rest of Sukkot.37

Not only that, but if someone is taking care of you, they may also eat out of the sukkah. Of course, if they can arrange to have someone take over for a while so that they can eat in the sukkah, they should do that.38

What if I Am Traveling?

If you’re on the road, can you eat your meals without a sukkah?

Depends.

If you’re on a business trip or the like, technically, you don’t have to seek out a sukkah.39 Of course, it’s a good thing to do since, as stated above, we like mitzvahs. Or at least just eat something that doesn’t require a sukkah.40

When you get to civilization, however, you’ll need a sukkah again.41

If you’re traveling for leisure, no excuse. Make sure before you leave that you’ll have a sukkah to eat in. No sukkah, don’t go. Or, keep to foods that don’t require a sukkah.42

And, as mentioned, the Chabad custom is to always try and eat in the sukkah, regardless of weather conditions and types of food being eaten. When else do you get to eat inside a mitzvah?