3. When on the third birthday is the Upsherinish ceremony to take place?[1]

Night versus day:[2] The Upsherinish ceremony and cutting of hair may take place either by the night or the day of the third birthday. Thus, there is nothing wrong with doing the ceremony the night of the birthday, especially if that is when people are able to attend, and indeed many are accustomed to do it at night for this reason.[3]

After Shacharis: When doing so by day, many are accustomed to do so in the morning, after Shacharis.[4] [The Baal Shem Tov cut the Alter Rebbe’s hair in the morning after Shacharis.[5] Likewise, the Alter Rebbe cut the hair of the Tzemach Tzedek in the morning after Shacharis.[6]]

Afternoon:[7] It is permitted to get a haircut in the afternoon, and hence certainly the Upsherinish haircut may take place then.

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[1] Shevach Habris 1:10; Nitei Gavriel 1:5

[2] Igros Kodesh 24:132 “Perform it on either the night of the 14^th, or the day of Erev Pesach”; 22:132; See Chanoch Lanaar p. 134; Shevach Habris 1:10 footnote 19 that he once witnessed by the Rebbe be an individual who brought his Upsherinish child by the distribution of Kos Shel Bracha which took place at night, and passed the Rebbe a scissor and asked the Rebbe to cut some the hair of his child, and the Rebbe did so.

In general, may one get a haircut at night? Some Poskim rule one is to avoid getting a haircut at night until daybreak. [Kaf Hachaim Falagi 27:12 and Moed Lecho Chaiy 6:7 based on Arizal; Zichron Moshe O.C. 251] The reason for this is because night time is a time of Gevuros, and hence if we avoid a haircut during Sefira certainly, and even more so, is it to be avoided at night. [Poskim ibid] Other Poskim however negate this ruling and conclude that one may get a haircut at night. [Pekudas Eliezer 493 based on Beis Oved and Mafteiach Eiynayim of Chida that Rav Chaim Vital got a haircut on the night of the 49^th of Omer, after saying Sefiras Haomer] Practically, the widespread custom is to allow haircuts at night. See Nitei Gavriel 1:5 footnote 10

[3] Shevach Habris 1:10 that so is the custom of Anash in France

[4] Shaareiy Yerushalayim 9; Sefer Hasichos 5700 p. 40; Likkutei Dibburim 3:481; Nitei Gavriel 1:5-6

[5] Likkutei Dibburim 3:481

[6] Sefer Hasichos 5700 p. 40

[7] See Shevach Habris 1:10 footnote 20; See Nitei Gavriel 1:5 footnote 10

May one get a haircut in the afternoon: The Arizal would refrain from cutting his hair after midday, and hence would only take a haircut before midday on Erev Shabbos. [Custom of the Arizal brought in M”A 251:5; Shaar Hamitzvos Parshas Kedoshim; Lechem Min Hashamayim p. 25; Nagid Umitzvah 2:113; Shulchan Aruch Harizal Tosefes Shabbos 11] Based on this some Poskim rule one is to beware to take a haircut prior to midday on Erev Shabbos. [Gr”a brought in Aruch Hashulchan 251:3; Kitzur Shulchan Aruch 128:15; Mateh Efraim 581:50; Mateh Efraim 625:11 “It is a Mitzvah Min Hamuvchar…”; Alef Lamagen 581:108 “Is a Mitzvah Min Hamuvchar”; Kaf Hachaim 260:13; 581:80 [proper to be stringent]] Furthermore, some Poskim rule that this applies even during the week, [All Poskim in coming brackets] as the time of Mincha may pass [M”A ibid; Machatzos Hashekel ibid; Ashel Avraham 568; Minchas Elazar 4:10] or because as the time of the afternoon is a time of Gevuros and the cutting of hair is the removal of Gevuros, and this mystically transgresses Lo Sachson Shur Bedisho. Moreh Baetzba 135; Moed Lekol Chaiy 3:3; [Lechem Min Hashamayim ibid; Pela Yoeitz Erech Giluach; Ben ish Chaiy Vayakehl 1:11, brought in Igros Kodesh 18:560] Other Poskim, however, rule that there is no issue with an afternoon haircut even on Erev Shabbos, and so is implied to be the opinion of Admur. [Admur 251:4; Aruch Hashulchan 251:3; Alef Lamagen 581:108] Practically, according to the approach that one may get a haircut at night, certainly one may do so in the afternoon. This certainly applies according to those opinions who hold that the entire issue of getting an afternoon haircut is only regarding the Mincha prayer, which does not apply to a three year old child.