2. On what day is the haircutting ceremony to take place?

One is to cut the child’s hair on the day that he turns three, which is on the day of his third birthday, as will be explained. [The Alter Rebbe had his Upsherinish take place on his third birthday, having his hair cut by the Baal Shem Tov.[1] Likewise, the Tzemach Tzedek had his hair cut on his third birthday by his grandfather, the Alter Rebbe.[2] Likewise, the Rebbe Rashab had his hair cut on his third birthday by his grandfather the Tzemach Tzedek.[3]] In the event that one could not or did not cut the hair on the third birthday, then it is to be cut at the next earliest opportunity [including even many years later[4]].[5]

Prior to third birthday:[6] The haircut is not to be performed at an earlier date, prior to age three, and is rather to be delayed until the birthday. [This applies even if the third birthday falls on a date in which haircuts are forbidden, nonetheless, we postpone the haircut rather than precede it.] This applies even if one desires to perform the haircut on Lag Baomer in Meron, nonetheless, it is not to be preceded to prior the third birthday.[7]

Post the third Birthday:[8] The haircut is not to be delayed past the third birthday and is rather to take place on the birthday itself. This is with exception to if the birthday falls on a day that haircutting is forbidden [see Halacha 3], in which case it takes place on the next permitted date that arrives. In the event that the haircut was delayed for whatever reason, then it is to be cut at the next earliest opportunity [including even many years later[9]].[10]

Delaying or preceding the Upsherinish to Lag Baomer:[11]  One is not to delay the Upsherinish for many weeks or months until Lag Baomer, although it may be delayed for some days in order to do it on Lag Baomer.[12] Thus, if the birthday falls before Pesach, it is not to be delayed until Lag Baomer.[13] At the very least, one is to begin the haircut before Pesach and then perform its finishing touches on Lag Baomer.[14] Likewise, one is not to precede the Upsherinish to Lag Boamer if the birthday falls out after Lag Baomer.[15]

Delaying the Upsherinish to Chol Hamoed:[16] Some Poskim[17] rule that even if the child was born before Yom Tov, one may even initially delay the Upsherinish until Chol Hamoed in order to increase the joy and festivity and doing so is even a Mitzvah. [However, the Rebbe negated any delay, as stated above.]

Q&A May one cut the child’s hair on his third birthday, but delay the festive celebration of the Upsherinish to a different day?[18] Yes. The main thing is that the cutting of the hair, and beginning of the formal education of Peyos and the other Mitzvos, begin on the 3rd birthday. The celebratory feast and party which publicizes the occasion to friends, family, and the community, can be held on another occasion, at a time and place that one sees fit. May one cut some of the child’s hair prior to age three [such as to trim the bangs which are bothering him, or to make him look pretty and nice]?[19] The custom of Jewry is not to cut any of the hair of the child until age three, even if the hair is a nuisance to the child or does not look nice. Must one cut all the child’s hair on the day of the Upsherinish, by his third birthday?[20] No. It is not necessary for all the child’s hair to be cut on that very day, and the main thing is simply that his Peyos be recognizable. Accordingly, if one is afraid that the child may get a cold if all of his hair is cut at once, [or if the child is protesting the haircut and making it difficult for it to be cut, or if one would like to save some of the hair for cutting on another occasion], then one is not required to give the child a full haircut.

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[1] Likkutei Dibburim 3:481

[2] Sefer Hasichos 5700 p. 40

[3] Sefer Hamamarim 5710 p. 163

[4] Nitei Gavriel Chapter 3:3 footnote 5 that so ruled Rebbe to a certain Baal Teshuvah

[5] Igros Kodesh 22:336

[6] Arugas Habosem 210; Maharam Brisk 2:98-99; Afrakasta Deanya 161; Toras Yekusiel 47; Shivim Temarim 68; Igros Kodesh Rayatz 2:438; Brought in Hayom Yom 4^th Iyar; Sefer Haminhagim p. 87; Igros Kodesh 7:235; 11:5, 60; 12:441; 14:39, 313; 18:361; 22:311 in name of Rebbe Rayatz; Likkutei Sichos 14:387; 32:246; Heichal Menachem 2:29; Mikdashei Hashem 1:76; Shevach Habris 1:1 and 13; Nitei Gavriel 1:2; 2:2

[7] Igros Kodesh 11:60; 14:39

Other customs: Some are accustomed to precede the haircut to Lag Baomer, even if it is prior to the third birthday. [Custom brought and negated in  Igros Kodesh 14:39]

[8] Toras Yekusiel 47; Afrakasta Deanya 161; 438; Brought in Hayom Yom 4^th Iyar; Sefer Haminhagim p. 87; Igros Kodesh 7:235; 11:60; 12:441; 18:361; 22:311; Heichal Menachem 2:29; Mikdashei Hashem 1:76; Igros Kodesh 11:5 [do it on birthday or the closest opportunity]; 11:60 and 14:39 and 220 [not to push off very long until Lag Baomer unless the Minhag is to do so]; 14:313; 18:361; 22:132 and 336 [not to push off at all]; Shevach Habris 1:2; Nitei Gavriel 2:2; See Rama Y.D. 245:8 that as soon as one’s child turns three years old he is to be taught the letters of the Torah

The reason: As on the third birthday there is a unique opportunity and auspicious time for the education of the child, and there is no telling if this can be recovered on a later date. [Rebbe ibid] In addition, why should one delay the drawing down of the holiness onto the child, which takes place upon cutting his hair and leaving him Peiyos. [Igros Kodesh Rebbe Rayatz 2:438; Igros Kodesh 14:39]

Other opinions: Some Poskim rule one may delay the Upsherinish past age three in order to have it performed on Chol Hamoed. [Ginas Veradim Gan Hamelech 62; Devar Moshe 1:45; Nechpa Bakesef 2:7; Mizbeiach Adama p. 7; Shulchan Gavoa 531:13; Shaareiy Teshuvah 531:7; Beir Heiytiv 531:7; Kaf Hachaim 531:30]

[9] Nitei Gavriel Chapter 3:3 footnote 5 that so ruled Rebbe to a certain Baal Teshuvah

[10] Igros Kodesh 22:336

[11] Shevach Habris 1:13; Nitei Gavriel 8:1

[12] Igros Kodesh 5:22; 11:60 and 14:39 and 220 [not to push off very long until Lag Baomer unless the Minhag is to do so]

Other customs: Some communities are accustomed to delay the Upsherinish until Lag Baomer, if the birthday falls within proximity of a number of months to Iyar. [See Igros Kodesh ibid that so is claimed to be the Minhag in Eretz Yisrael; Nitei Gavriel 12:2]

[13] Igros Kodesh 22:132

[14] Igros Kodesh 5:22

[15] Igros Kodesh 12:441; 14:39

Other customs: Some are accustomed to preceding the haircut to Lag Baomer, even if it is prior to the third birthday. [Custom brought and negated in Igros Kodesh 14:39]

[16] Shevach Habris 1:13

[17] Ginas Veradim Gan Hamelech 62; Devar Moshe 1:45; Nechpa Bakesef 2:7; Mizbeiach Adama p. 7; Shulchan Gavoa 531:13; Beir Heiytiv 531; Shaareiy Teshuvah 531:7; Kaf Hachaim 531:30

[18] Igros Kodesh 22:336; Shevach Habris 1:9

[19] See Arugas Habosem 210; Maharam Brisk 2:98-99; Igros Kodesh Rayatz 2:438; Brought in Hayom Yom 4^th Iyar; Sefer Haminhagim p. 87; Kisvei Rab Issac Shwei 1:272; Shevach Habris 1:3; Nitei Gavriel 1:2; See however Nitei Gavriel 2:3-4 that one may cut hair that is hurting the child, such as that is entering his eyes and the like

[20] Igros Kodesh 14:313; Shevach Habris 1:4