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The Rama
The Rama (Orach Chaim 426:2, citing the Maharil) states that one should not recite Kiddush Levanah on Motza’ei Shabbat heading into Yom Tov. The Mishnah Berurah (426:12) clarifies that it should also not be said on an ordinary Shabbat or Yom Tov night. The Mishnah Berurah notes that there are many Kabbalistic reasons for not saying Kiddush Levanah at this time. The Shulchan Aruch’s commentaries do not dissent from the Rama, and Sephardic Poskim agree (Rav Ovadia Yosef, Teshuvot Yabia Omer 8: Orach Chaim 41 and Yalkut Yosef Orach Chaim 426:33).
Mystical Explanations
One Kabbalistic explanation is that since Kiddush Levanah is such a joyous event, “Ein Me’arvin Simcha B’Simcha,” “we do not blur and dilute one Simcha with another.” A second mystical reason is that, since Kiddush Levanah is compared to greeting the Shechina, one elevates himself to the heavens. It is problematic to do so on Shabbat and Yom Tov due to the prohibition of exiting one’s Techum (boundary).
This last idea is of enthralling Hashkafic significance, as it expresses the immense power of Kiddush Levanah to transport us to the heavens and encounter the Ribono Shel Olam, Master of the Universe!
Non-Mystical Approaches
The Sha’ar HaTziyun (426:12) offers a non-Kabbalistic explanation based on the rabbinic prohibition to dance on Shabbat (Shulchan Aruch, Orach Chaim 339:3). The Sha’ar HaTziyun writes that since we are accustomed to dancing after Kiddush Levanah, we avoid Kiddush Levanah on Shabbat and Yom Tov evenings.
Another explanation stems from the various Bakashot, requests from Hashem, customarily included in Kiddush Levanah, which should be avoided on Shabbat and Yom Tov (Shulchan Aruch Orach Chaim 576:12).
The Ben Ish Chai (Vayikra 2:26) suggests that saying Shalom Aleichem counterbalances our saying “Tipol Aleihem Ameita VaFachad”, that our enemies should be struck with fear, at Kiddush Levanah. He notes that we may not say this on Shabbat or Yom Tov since we are forbidden to curse or excommunicate people on these special days.
The Sdei Chemed (Asifat Dinim, Ma’arechet Rosh Hashana 2:2) and Teshuvot Minchat Yitzchak (2:120:2) suggest (at least regarding Leil Shabbat) that the concern is about carrying on Shabbat. Since most do not know Kiddush Levanah by heart and it is customarily recited outside, there is concern that one may violate the prohibition of Hotza’ah (carrying) if we were to say Kiddush Levanah on Friday night. Similarly, the Mishnah Berurah (583:8) mentions this concern as a reason not to say Tashlich on Shabbat.
Exceptions
The Mishnah Berurah notes that the Halachic consensus permits reciting Kiddush Levanah on Shabbat or Yom Tov if it is the last opportunity to do so. Since the practice of avoiding Kiddush Levanah on Shabbat and Yom Tov is of later origin (the Maharil, a late Rishon), it has the status of a custom, which does not apply if it would cause one to miss a Mitzvah thereby.
The Aruch Hashulchan (Orach Chaim 426:10) states that when saying Kiddush Levanah on Shabbat or Yom Tov, one should omit the Tefillot and Bakashot normally added to Kiddush Levanah. He writes that one should limit Kiddush Levanah to the Bracha, implying that one should not dance on such occasions. Rav Mordechai Willig follows the Aruch Hashulchan.
If one needs to rely on a community Eruv to carry a Siddur outside to say Kiddush Levanah on a Friday night, it might be preferable to recite it inside. It is customary to say Kiddush Levanah outside when possible (Mishnah Berurah 426:21 and Yalkut Yosef Orach Chaim 426:23), but it is strongly recommended to avoid relying on a community Eruv when possible (Mishnah Berurah 345:23 and Yalkut Yosef Orach Chaim 345:4). Indeed, Rav Hershel Schachter permits saying Kiddush Levanah indoors to avoid relying on a community Eruv.
How Long Beforehand?
What if one has one more day after Friday to recite Kiddush Levanah – may one recite it on Shabbat lest the moon not be visible Motza’ei Shabbat? The Sha’ar HaTziyun (426:13) cites a dispute about this matter but does not resolve it. However, the Aruch Hashulchan (Orach Chaim 426:10) writes that in areas where it rains year-round, it should be said in such circumstances. He even relates that he permitted reciting Kiddush Levanah on several Friday nights, and that it rained on the subsequent Motza’ei Shabbat, thereby proving his ruling. Rav Oavdia Yosef (Teshuvot Yabia Omer 8 Orach Chaim 11) even permits reciting Kiddush Levanah on a Friday night when there are two days left to say it, lest one miss the opportunity to fulfill this precious Mitzvah.
Rav Hershel Schachter and Rav Mordechai Willig believe that one should say Kiddush Levanah on a Friday night only if it is the last night to say Kiddush Levanah. They agree that an exception might be made if the weather forecast strongly predicts rain for Motza’ei Shabbat or longer.
Soldiers in Tzahal (Israel Defense Forces), medical residents, or anyone working exceptionally long evening and night hours may also recite Kiddush Levanah on a Shabbat or Yom Tov night if they are concerned that their overwhelming responsibilities make these holy days the only times they can recite it.
Conclusion
The Minhagim our Chachamim (sages) have added over the generations, especially when influenced by Kabbalah, enhance our Mitzvah observance. However, we should never lose sight of our basic Halachic priorities. Observance of baseline Halacha is our primary responsibility. We must not risk failing to fulfill our basic Halachic obligations in the pursuit of honoring Minhagim and Kabbalistic ideas.
Thus, while we normally avoid saying Kiddush Levanah on Shabbat or Yom Tov, there are times we must.