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Beit Midrash
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Answer: Many early sources (Yerushalmi, Berachot 9:2; Sanhedrin 42a, in some texts; Rambam, Berachot 10:16; Shulchan Aruch, Orach Chayim 426:1) present the seeing of the moon as the presumed prompt for making the beracha, saying: "One who sees the moon …" This is despite the fact that we do not need testimony to know that it is there. If the beracha were a matter of the tzibbur, one could argue that if (most of) the minyan saw it, others could join the beracha if it began properly. However, Kiddush Levana is a beracha of the individual, and it is but a preference to do so among others (Be’ur Halacha to 426:2). Therefore, each individual needs the conditions to make the beracha. Usually, when it was seen moments before, it is likely to again be seen soon thereafter. However, there are still conceptual and practical matters to consider.
Is it critical to be able to see the moon, even in a case in which it will not be visible before the end of the beracha’s period? The Radbaz (I:341) says that a beracha made while the moon is covered is levatala, modeling it after Borei Meorei Ha’esh at Havdala. The Terumat Hadeshen (I:35) instructs that one should wait until Motzaei Shabbat for Kiddush Levana only if it leaves enough days for there not be concern of constant cloud cover. This implies that it can absolutely not be done with cloud cover.
Bemare Habazak - Rabbis Questions (654)
Rabbi Daniel Mann
429 - A Kohen Serving Others
430 - The Necessity to See the Moon Before Kiddush Levana
431 - Pressuring a Store to Take Back Purchase
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A major source that minimizes the need to see the moon is the Shut Maharshal (47), who says that a blind person (suma) can make the beracha. Many accept this opinion (see Mishna Berura 426:1), although many disagree (see Be’ur Halacha ad loc., VIII, OC 22). In contrast, a suma does not make the beracha on light at Havdala (Shulchan Aruch, OC 298:13).
However, many sources posit that the beracha is on the light. The p’sukim on the creation of the sun and moon stress the moon’s light-giving attribute (see Bereishit 1:14-18). In fact, the Rama (OC 426:1) says we must do Kiddush Levana late enough to not only see the moon but also benefit from its light. Even the Maharshal, who obligates a suma, requires benefit in terms of time and possibly place, just that not each person needs to personally benefit directly.
A few questions may hinge on how fundamental to the beracha the light or the benefit from it is. If it is like other berachot on seeing elements of nature and praising Hashem for creation (which the Rambam ibid implies), it would not seem critical that if, subsequently, during the beracha, it is covered (compare to the beracha on thunder/lightning). If the beracha is on receiving benefit from the light, it is more likely to need to continue throughout (see two opinions in Be’ur Halacha to 426:1). The accepted opinion is that one should believe it will last throughout the main beracha (until … mechadesh chodashim), but if one started, he can continue. There is also a machloket in the other direction, when there is enough light to benefit, but the moon is not clearly visible (see Shut R. Yaakov MiLisa, OC 7).
Arguably, the beracha’s nature might impact on a variation of your case – if the one who saw the moon made the beracha also intending to do so on behalf of those who did not. The beracha was valid due to the sighting, but the benefit did not extend to the one who listened. (The possibility of someone making the beracha and including a suma in it may be instructive – see Yabia Omer IX, OC 94 – whether or not it is a proof is beyond our scope.)
Bemare Habazak - Rabbis Questions Ask the Rabbi: Having a Non-Jew Build a Sukka and Assemble Arba’a Minim
Kuzari -Rabbi Ari Shvat Kuzari class 8- "Answering Questions on the Kuzari's Proof from Mass Revelation
Rabbis in Midrash
Lessons
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Kuzari -Rabbi Ari Shvat Kuzari class 9 - "Seeing is Believing" (parag. 21-30)
These paragraphs elaborate on the theme that seeing and knowing is better than any attempt to prove logically, and begins explaining the difference between Israel and gentiles.
Ein Aya Various Universal Stages of the Geula Process
Rav Kook examines the various stages of redemption, explaining how (in addition to the obvious oft-mentioned stages of ingathering the exiles, reviving the Hebrew language, army, state etc.) the messianic dream of world prosperity, the State of Israel and world unity can and are realistically and logically gradually coming true.
Kuzari -Rabbi Ari Shvat Kuzari class 8- "Answering Questions on the Kuzari's Proof from Mass Revelation
How do we know that the "claim" of mass revelation to 2,000,000 witnesses at Mt. Sinai is really true? This important class answers all of the questions skeptics ask about this claim of the Kuzari.
Ein Aya Armies Still Necessary for Balance & the War Against Wars
Rav Kook explains why the world was originally divided into the various seemingly contradicting ideologies and cultures, in order to develop each one respectively. Swords or armies symbolize how each respective ideology defends themselves, as well as deters their opposing ideologies and cultures. On the other hand, the messianic era will be one of peace, and Rav Kook explains the transition to that stage, which mankind is already undergoing.
The Land of Israel LGBT'S IN ISRAEL
The question was asked, how can one make Aliyah with the LGBT parades?
Kuzari -Rabbi Ari Shvat Kuzari class 7 - Five Accumulative Proofs of G-d
As a preparation for the Kuzari's classic proof of G-d from the mass-revelation at Sinai, we start here with 5 other directions to strengthen our belief which also contribute to what the Kuzari will present as well.
Ein Aya Muscle & Meaning: The Dual Nature of Gevurah (Physical Strength)
Is physical strength and fitness a necessity or an ideal? Although it if often totally overlooked among topics of Judaism, Rav Kook writes that it clearly is also a necessity to deter the many enemies of Israel, but even in Y'mot HaMashiach, in the Messianic era, to a certain extent, it's ideal continues even after our enemies will have been finished off.
