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“One takes leave of the previous year with Mincha of Erev Rosh Hashanah. One greets the new year with Maariv of the first night of Rosh Hashanah”
Tehillim prior to Maariv:
Before Maariv on the eve of Rosh Hashanah one is to read Tehillim. [See Introduction of this chapter]
The greatness of Maariv on the night of Rosh Hashanah:
In Kabala it is explained that the life force of the world which derives from the attribute of Malchus is in a state of withdrawal and renewal on the first night of Rosh Hashanah.
The form of Avoda of Maariv on the 1st night:
On the first night of Rosh Hashanah the form of Avoda required from a Jew in his prayer is one of bitterness and broken-heartedness over one’s lack of yolk of heaven and lack of faithfulness as a servant of G-d. This is to touch the core of his heart and he is to cry and supplicate before Hashem to accept him as His servant. This is the Avoda of Kabalas Ol Malchus Shamayim which must move his very essence. This Kabalas Ol is accepted above and causes great satisfaction before Hashem, and arouses His will for the Kingship.
The Maariv of the Chassidic Rabbeim:
The Chabad Rabbeim placed much emphasis in the evening prayers of the first night of Rosh Hashanah. The Rebbe Rashab would pray Maariv on the first night of Rosh Hashanah for 3-4 hours. He would Daven singing the Niggun of the Alter Rebbe [for Yamim Noraim] with a heart piercing voice. His prayer was accompanied by waves of tears. A crowd of Anash would gather to hear his prayers. The Rebbe Rayatz would Daven Maariv from the beginning of the night until approximately 12:30 at night. At times the prayer would take five hours. This custom dates back to the Alter Rebbe and was accustomed by all the Chabad Rabbeim.
The Alter Rebbe was accustomed not to speak throughout the entire night of Rosh Hashanah.
The Avoda required of the Chassidim:
From the above description of the Rabbeim it is understood that each and every Chassid must also exemplify the above intensity and spiritual investment into his Maariv prayer at least on some level.
The course of the Maariv prayer until Shemoneh Esrei follows the normal Maariv dialect of a weeknight. One however begins from Shir Hamaalos and not from Vehu Rachum.
For Shemoneh Esrei one Davens the special Rosh Hashanah dialect which includes the paragraphs of Vichein Ten Pachdecha. In Shemoneh Esrei one must remember to add the following statements: Zachreinu; Mi Chamocha; Vichein Ten Pachdecha; Hamelech Hakadosh; Ukesov; Ubesefer, Oseh Hashalom.
After Shemone Esrei of the evening services of Rosh Hashanah one says the psalm of Ledavid Mizmor Lahashem (Psalm 24) with intense concentration. It is recited prior to Kaddish Tiskabel and not directly prior to Aleinu. The Rebbe Rashab stated that the concentration applied while reciting the psalm of Ledavid creates the vessel that contains the blessing of one’s physical needs of the entire year. [Upon reciting this Psalm one is to intend on that his sustenance will not be lacking throughout the entire year. Some are accustomed to recite this Psalm also after Shacharis on Rosh Hashanah, prior to the last Kaddish. This is not the Chabad custom. Some have the custom to open the Aron upon reciting this Mizmor. This is not the Chabad custom. It is not our custom for the congregation to recite verse after verse following the Chazan.]
Wishing each other a good year:
It is customary [after the conclusion of Maariv] on the first night of Rosh Hashanah to wish one’s friend “Lishana Tovah Techasev Vesechasem”, [in the singular form]. [This can be said likewise at the conclusion of Maariv of the second night of Rosh Hashanah.] From after midday of the second day of Rosh Hashanah and onwards, we no longer bless each other with the word “Techasev” being the writing of the decree has already been finalized. [The custom is rather to say Gmar Chasima Tova.]
What is the dialect of the blessing that women are to wish each other?
A woman is to be told “Leshanah Tovah Tichtivi Vitichtimi…” in the female tense.
What dialect is to be used when blessing many people at the same time?
One is to say “Lishana Tovah Techaseivu Vesechaseimu” in the plural.
Sparks of Chassidus:
The Tzemach Tzedek once related: Two angels escort each Jew on the night of Rosh Hashanah. When these angels hear Jews blessing each other “May you be written and sealed for a good year” with a wholesome heart, they give a favorable recommendation and insist on a good and sweet year for that person.
The Rebbe’s custom:
The Rebbe would bless the congregation after Maariv of the first night of Rosh Hashanah. After Maariv the Rebbe turned around to the congregation and recited “Gut Yom Tov” three times and then recited “Leshanah Tova Tikaseiv Visichaseim” three times.
 Sefer Haminhagim P. 118 [English] from a letter of the Rebbe Rayatz
 Tanya p. 121 [Epistle 14]; Likkutei Torah Netzavim p. 106; Sefer Hamamarim 1924 p. 12; Likkutei Sichos 9/220
 Sefer Hamamarim 1943 p. 42-43
 See Otzer Minhagei Chabad p. 72
 Sefer Hasichos 1992 p. 13 footnote 19; The main length was in the prayer of Vichein Ten Pachdecha. [Otzer ibid] See Darkei Chaim Veshalom 706 however that states to lengthen in the first three blessings of Shemoneh Esrei.
 Likkutei Sippurim p. 201
 Sefer Hasichos 1941 p. 27
 Hatamim 2 p. 131
 Igros Kodesh Rebbe Rayatz 4 p. 7
 Igros Kodesh 4 p. 17
 See Sefer Hasichos 1992 ibid; Sefer Hasichos 1942 p.2; See Beis Rebbe 1 p. 22 footnote 3; Migdal Oaz p. 93 that the Ragatchover Gaon exclaimed in amazement that the Alter Rebbe, who was a true Gaon and philosopher, lengthened his prayer on the night of Rosh Hashanah. This custom was followed also by the Maggid of Mezritch who would Daven Maariv at night for many hours with much cry accompanied with it. [Sefer Hasichos 1942 p. 2]
 Likkutei Torah p. 85-86; Sefer Hasichos 1941 p. 26-27
 Sefer Hasichos 1992 p. 13 footnote 19
 Hisvadyos 1984 1 p. 26-27 “The reason for the custom to sing the Niggun of Ainu Malkeinu of the Alter Rebbe prior to each prayer on Rosh Hashanah is in order to mention the merit of our forefathers, the merit of the Alter Rebbe”.
Regarding Maariv: The Rebbe ibid stated in 1984 “Now that we are coming closer to the redemption, in which the Avoda of action is emphasized, there is no place for singing Avinu Malkeinu prior to this prayer being that Avinu Malkeinu is not recited during this prayer. For this reason Avinu Malkeinu was not sung before Maariv.” Nevertheless there was not one year similar to the next after this Sicha, in some years it was sung before Maariv and in others it was not. In 1992 it was only sung before Maariv on the second day of Rosh Hashanah. [Otzer Minhagei Chabad p. 58]
R”H that falls on Shabbos: Based on the Rebbe’s reasoning when the first day of Rosh Hashanah falls on Shabbos one should not sing the Niggun of Avinu Malkeinu prior to the prayers. Vetzaruch Iyun.
 Otzer Minhagei Chabad p. 58
 Siddur Admur “On Yom Tov one begins Shir Hamaalos”; Beis Yosef 237 in name of Kol Bo; Zohar p. 130
The saying of Shir Hamaalos is recorded in: Shiltei Giborim Brachos 2a; Elya Raba 237. The reason for its recital is because one may only say Kaddish over a set of verses. [Piskeiy Hasiddur 65] Alternatively it is said in order to recite Shema following words of Torah. [Elya Raba ibid]
 Siddur Admur; Siddur Shlah; Peri Eitz Chaim 25/7; Mateh Efraim 582/3; See Otzer Minhagei Chabad 107
Mizmor 81: Some are accustomed after Maariv to recite psalm 81 as many of its verses are connected to Rosh Hashanah. [Yifei Laleiv 5/1; Kaf Hachaim 582/25]
 Siddur Admur; Sefer Haminhagim p. [English]; Siddur Shlah; Peri Eitz Chaim 25/7; Otzer Minhagei Chabad 107
The Chabad custom: Although Admur in the Siddur writes to recite the psalm prior to Kaddish Tiskabel, nevertheless the Rebbe Rayatz gave a directive to recite it after Kaddish, prior to Aleinu, on the basis that this was the custom in Lubavitch. This custom is recorded in Hayom Yom p. 92 and Koveitz Lubavitch 5/71. Nevertheless in later years when the Minhagim were printed as part of the Machzor, the Rebbe Rayatz concluded that it is to be recited before Kaddish as is written in the Siddur. [See Otzer ibid]
 Sefer Ham’amarim 1927 p. 112; Sichas Chag Hapesach 1987; See also Mateh Efraim ibid “It is a Segula to effect that ones food not be lacking throughout the year”; Leshmoa Ozen p. 145; See Otzer Minhagei Chabad p. 68
 Kaf Hachaim 582/17 in name of Arizal in Peri Eitz Chaim 25/7
 Kaf Hachaim 582/15
 As it is not printed in Siddur Admur.
 Otzer Minhagei Chabad 108
 Otzer Minhagei Chabad 109; Darkei Chaim Veshalom 606
Other customs: Many have the custom that the congregation repeats verse after verse following the Chazan. This was also the Chabad custom in Eretz Yisrael. [Luach Kolel Chabad]
 Siddur Admur; 582/17 [the differences in the two sources will be noted in the footnotes]; Tur 582 that “So is the custom of Ashkenazi communities”; Rama 582/9
 Siddur Admur, omitted in 582/17; [See later footnotes regarding saying it on the second night]
 In 582/17 the wording is “that each and every person says to his friend”.
 In the Siddur Admur includes the word Techaseim and so is the Chabad custom [Sefer Hasichos 1991 Vol. 1 p. 37]
Ruling of Admur in Shulchan Aruch: In 582/17 Admur omits the word “Techaseim”.
Background: Whether the word “Techasem”, which means to be sealed, is to wished also on the night of Rosh Hashanah is discussed in the Poskim. Some Poskim rule it is not to be recited as even the Tzaddikim are not sealed in the book of life until Yom Kippur. [Asara Mamaros Mamar Chikur Hadin 2/10, brought in M”A 582/8; Levushei Serud ibid; Gra ibid] Others however rule that one is to say Techaseim, as Tzaddikim are sealed on Rosh Hashanah and one is to assume that his friend is a Tzaddik. [Magal Tzedek brought in M”A 582/8; Ran on Rosh Hashanah 16b; Chayeh Adam 139/5; M”E 582/26; Kaf Hachaim 582/63] In the Shulchan Aruch, Admur rules like the first opinion while in the Siddur he rules like the second. The Kaf Hachaim ibid concludes that even if Tzaddikim are only sealed on Yom Kippur it is is still best to already precede the blessing to Rosh Hashanah. The Rebbe’s father in Likkutei Levi Yitzchak [p. 210] writes that the general writing and sealing of the decree takes place on the night of Rosh Hashanah and it is only the details of the decree that are finally sealed on Yom Kippur.
Not to say the opposite order of Tikaseiv Leshanah Tovah: One is not to say the above phrase in the opposite order of Tikaseiv Leshanah Tovah or Tikaseiv Lechaim Tovim as this is the Roshei Teves of תל“ט which represents a curse. [Rav Avraham Azulai brought Birkeiy Yosef 582/13; Kaf Hachaim 582/61] However the Birkeiy Yosef ibid himself writes that this dialect may be said.
Lialter Lechaim Tovim Ulishalom: Some have the custom to conclude the blessing of “Leshanah Tova…” with the words “Lialter Lechaim Tovim Ulishalom”. [Alef Hamagen 582/26; Darkei Chaim Veshalom 706; see Otzer Minhagei Chabad 113]
 Sefer Haminhagim p. 118 as is the Nussach in Siddur Admur and 582/17; Likkutei Dibburim p. 43; See Otzer Minhagei Chabad 114 [as opposed to “Tikaseivu Vesecheseimu” in plural]; Regarding saying the words in plural when wishing more than one person-see Q&A!
 Taz 582/4 [“Say it also on the second night of Rosh Hashanah”]; Admur 582/17 writes until midday of the second day; Rebbe in Sefer Hasichos 1991 Vol. 1 p. 37 [Brought in Shaar Hamoadim Rosh Hashanah 22: “Perhaps there is room to say this statement also on the second night of Rosh Hashanah”] See Kaf Hachaim 582/64
The reason: As during the times of the Temple when the month was sanctified through testimony at times there were two days of Rosh Chodesh Tishrei, and the second day of Rosh Chodesh would be the first day of Tishrei, which is Rosh Hashanah. Therefore even today one should bless his friend on the second night. [Taz ibid; Levushei Sereud ibid; See Admur 600/4] The Rebbe ibid brings a letter from his father [Likkutei Levi Yitzchak Igros Kodesh p. 210] which writes that the general writing and sealing of the decree takes place on the night of Rosh Hashanah and it is only the details of the decree that are finally sealed on Yom Kippur. This general writing and sealing of the decree takes place on the night of Rosh Hashanah even before Tekias Shofar, although it is completion in a way of kindness and mercy is accomplished through Tekias Shofar which marks the conclusion of the writing. The Rebbe derives from this, and based on Admur 582/17, that perhaps one can wish his friend a good writing and sealing also on the second night of Rosh Hashanah, as the completion of the writing and sealing is only after Tekias Shofar of the second day.
Other opinions: Some Poskim rule one is not to bless his friend to be written or sealed on the second night of Rosh Hashanah. [Levush 596 [brought in Taz ibid]; Elya Raba 596/2; simple understanding of M”A 582/8 which is going on the Levush] The reason for this is because the Tzaddikim are written on the first day within the first three hours and it is hence improper to bless someone after this time, hence implying he is not a Tzaddik. [Levush ibid] Alternatively since we know the second day is not really the first of Tishrei, and is not the Biblical day of Rosh Hashanah, therefore we do not say it on the second day at all. [Elya Raba ibid]
Ruling of the Siddur: The wording of the Siddur “It is customary on the first night of Rosh Hashanah to wish…” implies that it is not said the second night, as rules the Levush; Elya Raba and M”A ibid. However the Rebbe ibid explains that Admur was referring to the custom, which is only on the first night, however from the letter of the law he leaves room for it to be said also on the second night.
Other opinions: The Levush ibid rules one is not to say it past three hours after the first day. The Elya Raba ibid says one is not to say it on the second day. The M”A ibid brings the Levush and says one may say it until midday. [see previous footnote]
 So is the widespread custom and so recited the Rebbe on numerous occasions both orally and in letters. [See Otzer Minhgaei Chabad p. 11-12,182, 195] At times this Nussach was even said after Yom Kippur! [See Otzer p. 258] In letters the Nussach usually was Chasima Vegmar Chasima Tova. [Otzer p. 12] See P”M 582 A”A 8 brought next. Vetzrauch Iyun from Sefer Hasichos 1991 Vol. 1 p. 37 which implies that one is no longer to say bless his friend with the Chasima.
Other Opinions: Some Poskim write one is to say “Leshanah Tova Tichatem” [P”M 582 A”A 8] Others say one is not to mention at all the Chasima as we assume that every Jew is a Tzaddik and has already been sealed on Rosh Hashanah. [Kaf Hachaim 582/65]
 P”M 582 A”A 8; Ruach Chaim 582/18; M”E 582/26; M”B 582/25; Kaf Hachaim 582/62;
The Chabad custom: The Rebbe stated the above dialect to a group of female students in the year 1979 and so was printed in one of the earlier publishings of Tehillas Hashem that girls are to be blessed in the above dialect, in female tense. [See Otzer Minhagei Chabad 114]
 Otzer Minhagei Chabad 114; This wording [in plural] was used by the Rebbe Rashab and Tzemach Tzedek as brought in Sefer Hasichos 1941 p. 27; 1945 p. 2-3. The Rebbe would also use the plural tense, although there were times it was also said in singular even when speaking to the pulic. However in pulic letters the dialect was in plural.
 Sefer Hasichos 5705 p. 1
 Otzer Minhagei Chabad 115 [see there regarding the custom of saying it three times]