I was fortunate to be able to learn about the beracha of “Leishev BaSukkah” with a group at my Shul over Yom Tov. Below are some of the salient points, with references to the sources, which are linked to here. In our usual style, the numbers in the notes below correspond to the numbers of the sources linked to above, which can be learned alongside the notes to create a full learning experience. As an added bonus, all of the sources have English translation alongside the Hebrew.

1) The Gemara (Source 1) presents a three-way argument regarding how many times a person should make the berachot on the sukkah (“Leishev BaSukkah”) and the lulav (“Al Netillat Lulav”) over the course of Sukkot. Shmuel says that the beracha on the sukkah should be made only once each year; because the mitzvah continues uninterrupted for seven straight days, night and day, there is never an opportunity or a need to make any additional berachot of “Leishev.” (Shmuel expresses this as לא מפסקי לילות מימים – there is no [meaningful] separation between night and day.) Lulav, on the other hand, which is not taken at night, requires a new beracha when the mitzvah is renewed each morning (מספקי לילות מימים). The Gemara then presents two versions of Rabbi Yochanan’s opinion, the first by Rabba bar bar Chana and the second by Ravin. According to the first version, Rabbi Yochanan felt that the beracha on sukkah should be made all seven days, because it is a Torah commandment even outside of the Beit Hamikdash. Lulav, on the other hand, which is only a Rabbinic commandment outside of the Beit Hamikdash on the second through seventh days of the holiday, should have a beracha made only on the first day, when it is a Torah commandment. (This is difficult given that we say many berachot on Rabbinic mitzvot; Chanukah and Megillah come to mind.) The second version of Rabbi Yochanan has it that the berachot on both sukkah and lulav should be made all seven days. No reason is given for this final opinion, and the Gemara concludes that we should follow the first version of Rabbi Yochanan. (See the chart at the end of Source 1.)

Although we all know experientially that we follow the second version of Rabbi Yochanan and make a beracha on both lulav and sukkah all seven days of Sukkot, it is fascinating how this Halacha has (or has not) come down to us. The Ein Mishpat on the Gemara, which notes whose opinion is accepted as the Halacha and sends us to the right location in the Rambam and Shulchan Aruch to learn more, puts the relevant superscript letter before the second version of Rabbi Yochanan (seven days for both mitzvot). However, the place where it tells us to go in the Shulchan Aruch (Orach Chaim סימן תרלט – 639; below but not in the sources) not only doesn’t mention the beracha at all but seems suspiciously to sympathize with Shmuel’s opinion (a beracha for sukkah only on the first day):

,כיצד מצות ישיבה בסוכה? שיהיה אוכל ושותה [וישן ומטייל] [טור] ודר בסוכה כל שבעת הימים, בין ביום ובין בלילה כדרך שהוא דר בביתו בשאר ימות השנה. וכל שבעת ימים עושה אדם את ביתו עראי, ואת סוכתו קבע …

What is the mitzvah of living in the sukkah? That a person should eat and drink (and sleep and spend time – Tur) and live in the sukkah all seven days, both in the day and in the night, in the same way that he lives in his house the rest of the days of the year. And all seven days, he should make his house his temporary abode, and his sukkah his main abode.

The seemingly extraneous verbiage that a person should live for “seven days, day and night” in the sukkah seems to mirror Shmuel in the Gemara that “לא מפסקי לילות מימים” – “there is no meaningful separation between night and day” when it comes to the mitzvah of sukkah. If the mitzvah continues uninterrupted for seven days, why indeed should we make more than one “Leishev?”

There is further evidence that the Shulchan Aruch has an affinity for the opinion of Shmuel. Later on in סימן תרסב (Siman 662) the Shulchan Aruch has this to say about the beracha on the lulav:

ביום שני מברך על נטילת לולב וכן בכל שאר ימים:

On the second day of Yom Tov, a beracha is made on the lulav, and the same is true for all of the rest of the days (of Sukkot).

And yet just one siman before that, the Shulchan Aruch says this about the beracha of “Leishev” on the sukkah:

בליל יום טוב שני אומר קידוש וזמן אחריו מיד ואחר כך ברכת סוכה [זו דעת הרא”ש וכן ראוי לנהוג]:

On the second night of Yom Tov, one says Kiddush, and She’hechiyanu immediately afterward, and then the beracha on the sukkah.

Naturally one makes the beracha of “Leishev” on the second night, because the second night of Yom Tov always mirrors the first night outside of Israel. But this would have been an excellent opportunity for the Shulchan Aruch to say that we make a “Leishev” every day of Sukkot, just as he goes on to say about the beracha on the lulav one page later. After all, both are subject to the same Talmudic dispute! Yet the Shulchan Aruch never informs us of this fact. Further complicating matters is the fact that the Tur says clearly (Source 9) that we make a beracha of “Leishev” every time we enter the sukkah, and the Beit Yosef (Source 10) appears to agree. Yet in the Shulchan Aruch, the Beit Yosef himself is silent on the matter. He only mentions “Leishev” one other place (Source 11), but again not in the context of how many days it is said.

It is hard to believe that the Shulchan Aruch would have taken as a given something that the Tur (and many other Rishonim; see Sources 2, 3, 4, 5, 6, 7, and 8) needed to state explicitly and that the Gemara leaves open to dispute. Could the Shulchan Aruch perhaps be partial to Shmuel’s opinion? After all, Shmuel’s reasoning (which, as we saw, the Shulchan Aruch seems to reference in 662) is more compelling than Rabbi Yochanan’s distinction between Torah and Rabbinic commandments, since we make many berachot on Rabbinic mitzvot. And the second version of Rabbi Yochanan doesn’t come with any reasons at all. Shmuel’s reasoning about the continuance of the mitzvah for seven complete days is air-tight by comparison. צריך עיון.

2) Based on the Gemara, the beracha of “Leishev” would only be said either once (Shmuel) or seven times (Rabbi Yochanan) over Sukkot. Tosafot (Source 2) is the first to extend the recitation of the beracha to the nearly limitless times that one may enter his sukkah over the course of the holiday. They take this leap based on a comparison to Tefillin, which, although a daily mitzvah, nonetheless require a new beracha each time they are put on over the course of the day. Likewise, reasons Tosafot, although the beracha of “Leishev” is a daily beracha, it can and should be said as many times as one does the mitzvah of entering the sukkah for virtually any reason during the day – eating, drinking, sleeping, learning, spending time. I find this comparison, which other Rishonim adopt as well (see Sources 4 and 10), to be wanting. First of all, the need to extend the beracha on sukkah from once to multiple times per day is based on the assumption that Shmuel and Rabbi Yochanan meant to require the beracha on sukkah once per day in the first place. This would be true if Shmuel had indeed meant that the beracha should be said once on the first day of the holiday and Rabbi Yochanan had either agreed or felt that it should be said once every day. In reality, though, Shmuel may have meant that the beracha should be said multiple times on the first day, while Rabbi Yochanan (in his second version) felt that the beracha should be said multiple times every day of the holiday. Or Shmuel may have felt that the beracha should be said only once on the first day, but Rabbi Yochanan felt that it should be said multiple times on the first day (as not saying it at all on the later days would not preclude its being said multiple times on the first day), or multiple times every day. Either way, we may not need this comparison to Tefillin altogether, because that comparison is based on what may be a faulty assumption, namely that Shmuel and Rabbi Yochanan are discussing not merely the number of days that the beracha on sukkah should be said, but also the number of times per day that it should be said. Moreover, why choose Tefillin? A comparison could just as easily be made to the mitzvah of learning Torah, which is said only once per day even if a large amount of time separates instances of fulfilling the mitzvah, and in that case the beracha on the sukkah would similarly be made only once per day, even if Shmuel and Rabbi Yochanan really had meant to express the number of times per day (one) that the beracha is said! צריך עיון.

3) The רא”ש (Source 3) presents a fascinating dichotomy between the Halachic ideal and reality in regard to the issue of this beracha. Ideally one should say the beracha every time he enters the sukkah for any reason, with the further implication that the beracha be said before one sits down, since once one has sat down he has done the mitzvah and it is now too late to say the beracha. (Berachot must be made prior to the fulfillment of a mitzvah – עובר לעשייתן; hence if one has fulfilled his mitzvah simply by sitting down, it is now too late to say the beracha.) However, the Rash tempers this ideal with the reality that most people associate the mitzvah not with entering the sukkah but with eating in it, and thus it is not too late to make the beracha once one has sat down, as long as he has not yet eaten. This is an extraordinary example of Halacha being shaped by common perception rather than by the strictest of Halachic ideals, and it resurfaces in an argument between the Rambam and Ra’avad (Source 5). The Rambam feels that it is very important to say the beracha of “Leishev” before one sits down – he emphasizes this point twice in the Halacha before us on the page. The Ra’avad, however, feels that הישיבה אינה אלא על דעת האכילה, וכל זמן שאינו אוכל, הברכה עובר למצוה היא באמת – “The sitting down is only with the intention to eat; so as long as he has not yet eaten, the beracha is still considered to be ‘prior to the mitzvah.'” Again, the popular misconception that the mitzvah is not to enter or sit down but rather to eat in the sukkah shapes both the recitation of the beracha at all, as well as its timing.

Interestingly, the Shibolei Haleket (Source 8) presents another reason to allow one to make the beracha even after sitting down. He explains that the rule requiring one to make a beracha prior to the fulfillment of the mitzvah – עובר לעשייתן – mandates only that one not make the beracha after he has done the mitzvah. However, the beracha may be made during the mitzvah, as with one who has already sat down but is now still sitting and thus still fulfilling his mitzvah. In our case, then, one could theoretically only not say the beracha once he has gotten up to leave the sukkah. See Mishna Berurah (Source 12, final paragraph) regarding one who realizes as late as after Birkat Hamazon that he neglected to say “Leishev” being able to say the beracha anyway because he is still fulfilling a mitzvah by sitting in the sukkah. This reverts to the original perception of the mitzvah as more than simply eating, so the Rash would be pleased.

4) Rav Hai Gaon (quoted in Sources 3, 7, and 10) assumes that one who visits his friend’s sukkah makes a beracha of “Leishev” whether he is planning to eat there or not. It is tempting to believe that this is simply a case of Rav Hai’s having lived at an earlier time in history when the beracha was made whether one was entering a sukkah to eat or to do any other activity. However, this would make Rav Hai’s statement regarding a friend’s sukkah in particular superfluous, since it would be true even in one’s own sukkah. Thus Rav Hai must have felt that ordinarily the beracha is said only when one will be eating, but that this case is different for some reason. I would submit that the difference is that in one’s own sukkah, the (mis)perception is that the overarching primary function is one of eating; if our subject does not eat now, he will eat at some point later. But in his friend’s sukkah which he is only entering temporarily and without any desire to eat, the entire period of residency will come and go without eating ever having been on the agenda, and we thus revert to the original law that entering for any reason at all necessitates a beracha of “Leishev.” The friend’s sukkah exists for the visitor only in the realm of spending time, but entirely outside the realm of eating. The case of the friend’s sukkah is essentially a case study in what would happen if one’s own sukkah were not in any way planned to be used for eating. The Mishna Berurah (Source 12, beginning of paragraph #48) picks up on this theme by discussing the case of a person who plans to fast for an entire day of Sukkot: דדוקא כשאוכל פת, סבירא ליה להנהו פוסקים שמברך על עיקר חיוב הסוכה ופוטר כל הדברים הטפלים. אבל כשאינו אוכל, לא שייך זה. “Yet it is only when he eats bread that … this central aspect of being in the sukkah exempts the secondary aspects. But when he is not eating, this is not relevant!” In other words, in a situation where eating will not take place – either because he is fasting or, in Rav Hai’s case, because he is visiting a friend with no intention to eat – there is no eating to exempt sleeping or spending time. In such a case we revert to the original law (preferred by the Rash in Source 3) that one’s entering for any reason warrants a beracha. We can only honor the perception of eating being primary if eating is to take place at some point. If it is not on the agenda, a “Leishev” should be made upon entering, and perhaps even before sitting down.

5) If one built two sukkot, one for eating and one for sleeping (more common in Israel than abroad), it would appear based on what we have said until now that he should make a “Leishev” before sleeping in the sleeping sukkah, since the sleeping sukkah exists for him entirely outside of the realm of eating, and there is thus no eating to exempt his sleeping from the beracha. However, this may not be the case. The Rash (Source 3) presents an additional reason to exempt sleeping from the beracha, namely that one may not actually fall asleep and his beracha will then be a beracha le’vatalah, an unnecessary beracha. This is hard to understand. The beracha of “Leishev” does not mention sleeping specifically, so the beracha would seem to be relevant even if he merely spent time resting the entire night without ever falling asleep. Recall that according to all Rishonim, the theoretical construct of the beracha is to be said even just for entering the sukkah with the intention of spending some time, which would certainly be accomplished by our restless insomniac. The usual beracha of “Hamapil,” on the other hand, which mentions falling asleep explicitly, seems more nearly to pertain to the problem of having been a beracha le’vatalah if one does not fall asleep at all or even for more than just a few moments. צריך עיון on both counts.

There is more to explore in the sources – ואידך זיל גמור. Chag Sameach, and may be zocheh to be יושבים in the fallen sukkah of Dovid very soon.