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According to Rashi to Devarim 3:24 (here):

לאמר TO SAY (i.e. that God should say) — This is one of the three occasions where Moses spoke before the Omnipresent: I will not let You go until You tell me whether You will fulfill my request or not (Sifrei Devarim 26:9; cf. Rashi on Numbers 12:13).

What were the three occasions in which Moshe begged to enter אֶרֶץ יִשְׂרָאֵל‎? Where can they be found?

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It’s not three places that Moshe begged to enter Israel. It’s three places that Moshe speaking to Hashem is described using the word לאמר, which the Midrash interprets as Moshe demanding a response.

Other places where this phenomenon is found include:

  • Shemot 6:12
  • Shemot 17:4
  • Bamidbar 12:13
  • Bamidbar 27:15

As all these places are listed in the Sifrei to this verse in Devarim, it’s not totally clear to me which ones Rashi means to include in his count of three.

However, I do see that Rashi brings this idea in his commentary to the following three places only, possibly implying that these are the three he is referring to:

  • Bamidbar 12:13
  • Bamidbar 27:15
  • Devarim 3:24

Note also that in Rashi’s comments to Bamidbar 12:13, he quotes R. Elazar b. Azaryah as counting four instances (omitting Shemot 17:4).

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The other instances relate to entirely different topics, and are enumerated in Rashi's commentary to Numbers 12:13 as follows:

ר׳ אלעזר בן עזריה אומר בארבע מקומות ביקש משה מלפני הקב"ה להשיבו אם יעשה שאילתו אם לאו כיוצא בו וידבר משה לפני י"י לאמר הן בני ישראל וגו' מה תלמוד לאמר השיבני אם אתה גאלם אם לאו עד שהשיבו עתה תראה כיוצא בו וידבר י"י אל משה לאמר יפקד י"י אלהי הרוחות וגו' כיוצא בו ואתחנן אל י"י בעת ההיא לאמר השיבו רב לך

R. Elazar Ben Azariah says that in four places Moses requested of God to respond to him whether his question would be answered or not. Similarly "and Moses spoke before God saying 'they are the children of Israel' etc.". What does it mean? "Answer me if You will redeem them or not", until He responded "now you shall see". Similarly "and Moses spoke to God saying 'let God the god of spirits appoint' etc." Similarly "'and I implored God at that time saying'", he answered him "'it is sufficient for you'".

Note that there are actually four instances, namely our case here, asking whether the Israelites would be redeemed, asking whether Miriam would be healed or not, and asking whether a leader would be appointed or not.

Interestingly, the Sifrei on the verse here mentions a fifth such instance when Moses asked God if he would fall into the hands of the rebellious Israelites when they demanded water. See the supercommentaries to Rashi for some attempted resolutions to the differing numbers provided.

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  • Have you ever wondered why Aaron never asked to enter Israel. If you ask this as a question I shall give my original answer. Unless you have your own. – interested Dec 7 '20 at 11:17

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