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Apple dipped in honey:
On the first night of Rosh Hashanah the custom is to eat a sweet apple with honey at the beginning of the meal. A blessing of Haeitz is to be recited prior to eating the apple. [Immediately] after [reciting the blessing of Haeitz, prior to eating the apple], one is to say “Yehi Ratzon Milifanecha Shetichadeish Aleinu Shana Tova Umetuka”. [After concluding the Yehi Ratzon one immediately proceeds to eat the apple.]
Is the apple to be eaten before or after Hamotzi?
Is one to recite the blessing over the apple first even if there are Shiva Minim on the table?
Some Poskim rule one is to first eat the apple dipped in honey even if there are other fruits of the seven Minim on the table. However other Poskim rule that if there are fruits of the Shiva Minim on the table then their blessing is to be preceded. Practically the Chabad custom is to precede the blessing of the apple even if other fruits of the Shiva Minim are present.
When is the Yehi Ratzon to be recited over the apple?
Some Poskim rule one is to recite the Yehi Ratzon only after eating part of the apple. Others however rule that the Yehi Ratzon is to be recited after the blessing, prior to eating the apple. Practically the Chabad custom is to recite the “Yehi Ratzon” after the blessing prior to the eating.
Is the apple to be eaten also during the meal of the second night of Rosh Hashanah?
The Chabad custom is to eat the apple only on the first night of Rosh Hashanah. See next Halacha in Q&A for all the opinions on this matter.
Having in mind to include other fruits in the blessing:
Upon reciting the blessing of Haeitz over the apple one should have in mind all the fruits to be eaten during the meal, and not say a separate blessing over them later on. This includes fruits eaten as dessert prior to Birchas Hamazon. One does not recite another blessing over the dessert even if he is eating the dessert in another home, prior to Birchas Hamazon.
After eating the Challah after Hamotzi, one is to eat a sweet apple dipped in honey saying first the blessing on the apple and immediately afterwards the “Yehi Ratzon” printed in the Machzor. After saying the Yehi Ratzon one is to eat the apple. One is to first eat the apple even if there are other fruits of the seven Minim on the table. One should have in mind all the fruits to be eaten during the meal, and not say a separate blessing over them later on. This includes fruits eaten as dessert prior to Birchas Hamazon.
Sparks of Kabala
The meaning behind the apple:
Chakal Tapuchin Kadishin:
The apple represents the “orchard of apples” which is well known in Kabalistic literature.
The three senses:
The significance of the apple is as follows: An apple contains three benefits: Smell; Taste and Sight. These three senses represent the three channels of blessing in Banaiy [children], Chayaiy [Health] and Mezoni [livelihood]. Eating the apple on the night of Rosh Hashanah serves as a good omen to these three channels of blessing.
Sweetens the Gevuros:
It is customary to eat an apple after drinking wine in order to prevent the wine from causing damage. Some even initially enter apple into their wine for this reason. Thus we see that the apple serves as a sweetener to the wine which comes from Gevuros. For this reason we eat apple on this night in order to sweeten all the severities.
The beginning of the winter:
The Zohar states that all the fruits derive from Malchus/Nukva with exception to the apple which derives from Tiferes/Duchra. Now the level of Malchus shines during the summer while the level of Tiferes shines in the winter. Thus since the beginning of the winter is Tishrei, therefore we eat an apple on the night of Rosh Hashanah.
The Midrash states that the apple tree does not give off shade. This means to say that its shade is very minute. In Kabala shade represents a contracted level of Makif revelation. All the fruit trees receive from this level with exception to the apple. The apple is rooted in Tiferes and receives directly from the level of Emes of which there is no shade or contraction. Based on this I heard in the name of Admur [the Tzemach Tzedek] that this is the reason we are accustomed to eat the sweet apple in honey on the first night of Rosh Hashanah, as Tishrei is the seventh month which corresponds to the Tikkun of Emes. In Tishrei Atzmus is revealed without any contraction and through our Teshuvah in this month we reach Atzmus. We thus eat a fruit that is rooted in the level of Emes as a symbol of this matter.
The meaning of Honey:
Honey comes from Gevurah. Nevertheless honey is a sweetened Gevura [Gevura Shebichesed] and thus has the ability to sweeten all other items. It is able to preserve all items preventing them from deteriorating as it compacts the item and prevents its four Yesodos from separating. Furthermore it has the power to eventually turn the item it is preserving into actual honey. It thus is able to turn the bitter into the sweet in play of the Avoda of Is-hapcha.
 Siddur Admur; 583/1 [“There are those that are accustomed to eat a sweet apple dipped in honey”]; Sefer Haminhagim p. 118; Tur 583; Rama 583/1; Kisvei Arizal [Peri Eitz Chaim Tefilos R”H 7] The custom to eat the apple with honey is not mentioned in the Gemara [Horiyos 12a]
 Siddur; The wording in 583/3 is “There are those that are accustomed”.
 So adds Rama 583/1 and Admur in both 583/1 and Siddur. This is seemingly coming to exclude a sour apple.
 The Rebbe was accustomed to cut the apple and dip it three times into the honey. [Otzer Minhagei Chabad 137]
Sugar: Some Poskim write that it is better to use sugar water than to use honey as honey comes from Gevurah, while white sugar is Chesed. [Yifei Laleiv 3/1; Ben Ish Chaiy Netzavim 4 [“cooked in sugar water”]; Kaf Hachaim 583/17; See also Kaf Hachaim 582/4; See however Torah Or Shemos p. 101 in Hosafos of the greatness of honey and how it is Gevura Shebichesed, or sweet Gevuros, and has the ability to sweeten all other items in play of the Avoda of Ishapcha.]
 Admur in Siddur; Tur 583; Sefer Haminhagim p. 118; omitted in 583/1; See Q&A!
 Siddur; 583/1; M”A 583/1; Darkei Moshe; Mateh Yehuda; Machatzis Hashekel on M”A ibid; Mamar Mordechai 583/2; Shaareiy Teshuvah 583/2; Kaf Hachaim 583/13
The reason one says the blessing on the apple and not on the honey: One is to say the blessing of the apple and not the honey as the honey is secondary to the apple. [583/1 and all Poskim ibid; See Drashos Mahril R”H for a discussion of whether the apple or the honey is the main food. He concludes that the apple is the main food and hence Haeitz is recited] Furthermore one already ate the Challah with honey prior to eating the apple and it is hence already exempt from a blessing. [Kaf Hachaim ibid]
Other opinions: Some Poskim rule that due to doubt one is to eat the apple and honey with the bread, in which case a blessing is avoided according to all. [Shvus Yaakov 2/27] The Shaareiy Teshuvah ibid negates his opinion.
 Sefer Haminhagim p. 118; See Q&A for the full analysis on this subject!
Ruling of Admur in Shulchan Aruch: Admur rules in 581/3 that the Yehi Ratzon is said after the initial bite as it is forbidden to make an interval between the eating and the blessing. See Q&A!
 Siddur Admur
Nussach in Admur 583/1: In 583/1 Admur writes the following Nussach: One is to say “Tischadesh Aleinu Shana Metuka”. This follows the Nussach of the Rama 583/1 and Abudarham R”H. The difference is in two matters: 1. Tischadesh versus Tichadesh; 2. Yehi Ratzon is omitted. Vetzrauch Iyun why Admur in 583/1 omitted the words Yehi Ratzon, in contrast to what he himself writes earlier in ibid regarding the other Simanim. See however Piskeiy Teshuvos 583 footnote 3 that negates the custom of saying the Yehi Ratzon only by the apple and not by the other Simanim as the apple is not written in the Gemara. Thus perhaps Admur ibid learns that it is less of a status than the other Simanim and hence the Yehi Ratzon is not recited by the apple.
Yehi Ratzon with Hashem’s name: According to Admur in the Siddur [and so is implied from his Shulchan Aruch 583/1] the Yehi Ratzon is recited without mentioning G-d’s name. [See Shaar Hakolel 42/2 that even within the Siddur of Admur there are a number of Nuschaos, some with Hashem’s name in the Yehi Ratzon, however he concludes that the correct Nussach of Admur is without Hashem’s name. He writes that this follows Rav Haiy Gaon however in truth Rav Haiy Gaon omits the Yehi Ratzon completely.] So rules also Kitzur SH”A 129/9; Darkei Chaim Veshalom 707 that Hashem’s name is not recited. The M”E 583/2 omits Hashem’s name by the Yehi Ratzon of the apple although he mentions it by the other Simanim. There are Poskim that write one is to recite the Yehi Ratzon over the apple with Hashem’s name [i.e. Yehi Ratzon Milifanecha Hashem Elokeinu Velokei Avoseinu…”]. [Siddur Yaavetz, Beis Yosef, Kol Bo; Abudarham; M”B 583/2; Siddur Shlah; Siddur Arizal]
Other Nuschaos: In the Siddur it says “Milifanecha”. This is omitted in other Nusschaos. [Darkei Chaim Veshalom ibid] In the Siddur Admur writes Tichadeish and so writes Siddur Yaavetz; Kitzur SHU”A 129/9; majority of Machzorim. In other sources it says Tischadeish. [Admur in 583/1; Rama 583/1 in name of Abudarham; M”E 583/1]
 M”E 583/1 [don’t delay at all between the Kiddush and Hamotzi]; Admur in Siddur [“beginning of meal”]; Tur 583 [“in beginning of meal”]; Darkei Moshe 583/3 [say blessing on apple during the meal]
 Igros Kodesh 3/209 [printed in Sefer Haminhagim p. 203-English; Shulchan menachem 3/85]; Custom of Rebbe Rayatz in 1948, recorded in Otzer Minhagei Chabad 136; However in Sefer Hasichos 1945 p. 4 the Rebbe Rayatz stated that the custom in Lubavitch was to eat the apple with honey after Kiddush, prior to Hamotzi. In Igros Kodesh 29/62 the Rebbe explains that “our custom follows the wording in the Siddur and the witnessed practice of the Rebbe Rayatz unlike Sefer Hasichos ibid”. Until the publication of this letter of the Rebbe and Sefer Haminhagim ibid the custom amongst Anash was like Sefer Hasichos, to eat the apple before the meal. See Igros Kodesh 21/98; Heichal Baal Shem Tov 34/182 .
The reason: As it is best to proximate the Kiddush to Hamotzi as much as possible. This is besides for the fact that when a food is dipped in honey one is required to wash his hands prior to eating it [158/3; Seder 20], and hence it is better to delay it until after one has washed for bread. [Igros Kodesh ibid; Glosses of Rav Raskin on Siddur p. 512]
 Drashos Mahril R”H [“after Kiddush”]; Siddur Arizal of Rav Shabsi [“immediately after Kiddush”]; Darkei Chaim Veshalom 707; Sefer Hasichos ibid that so was custom in Lubavitch; Ketzei Hameteh 583/1
 Siddur Arizal of Rav Shabsi [eat the apple immediately after Hamotzi]; custom recorded in Kaf Hachaim 583/13
 The reason: The apple is eaten first in order to serve as a good omen. [Kaf Hachaim ibid] Based on this one can say that the other fruits do not receive any precedence over the apple, as the apple is Chaviv and whenever one has two fruits and one is Chaviv, precedence is not given to the 7 Minim over the Chaviv. [See Admur Seder 10/8 ]
 Luach Eretz Yisrael; custom recorded in Kaf Hachaim 583/13 and final Seder of Kaf Hachaim 583/25 [that dates come first as they are sweet and from the Shiva Minim]; Opinions in Piskeiy Teshuvos 583/2; Ben Ish Chaiy Netzavim 4 lists the apple as the last food to be eaten
 Luach Kolel Chabad based on directive of Rebbe; Otzer Minhagei Chabad 140; The Rebbe in 1970 asked for the Rimonim to be brought to the table and only after they were brought did he recite the blessing of Haeitz on the apple. [Otzer ibid]
 Admur 581/3; M”A 583/2; Elya Raba 583/3; P”M 583 A”A 2; M”B 583/4; Kitzur SHU”A 129/9; M”E 583/1; Siddur Haarizal; Kaf Hachaim 583/16; The Chayeh Adam 139/6 and Mamar Mordechai 583/3 write to eat a small part of the apple without honey and then dip a second piece in honey and recite the Yehi Ratzon. [brought in Kaf Hachaim 583/13 and 16] The Sdei Chemed R”H 2/4 records the above option as well as another alternative option: Eat a different fruit with Haeitz and then say the Yehi Ratzon on the apple.
 The reason: As it is forbidden to make an interval between the eating and the blessing. [Admur ibid; Poskim ibid]
How much of the fruit is one to eat? Admur and Poskim ibid state “After the initial eating”. This implies that one is to recite the Yehi Ratzon immediately after heating and swallowing the first bite of the apple, and he is not to wait until he eats a full Kezayis and the like. [Alef Hamagen 583/8; Misgeres Hashulchan 129/6; Sdei Chemed R”H 2/4 in name of Orach Chaim and Mamar Mordechai]
Bedieved: Even according to this opinion, Bedieved if one said the Yehi Ratzon prior to the initial eating he nevertheless fulfills his obligation of the blessing. [M”A 583/2; Elya Raba 583/3; M”E 583/1; Mamar Mordechai 583/3; Ashel Avraham Butchach 583; See Admur 167/9; 206/3; Seder 9/1; Ketzos Hashulchan 37/7; However see Rebbe in Igros Kodesh 3/140 that leaves the wording in Admur 583/3 with a Tzaruch Iyun.]
 Machzor Maglei Tzedek brought in M”A 583/2 [The M”A brings the opinion of Maglei Tzedek that one first says Yehi Ratzon and then eats the fruit although he himself concludes against this opinion]; This custom is also recorded in Sdei Chemed R”H 2/4 in name of Chemdas Yamim 4/6
 Igros Kodesh 3/140 [brought in Shaareiy Halacha Uminhag 2/239; Shulchan Menachem 3/86]; Sefer Haminhagim p. 118; Hayom Yom p. 92; Reshimos 4 p. 8 [Was the custom of Rebbe Rayatz and Rebbe Rashab. The Rebbe Rayatz told the Rebbe that it is a directive for the public and it was therefore publicized in Hayom Yom.] See Otzer Minhagei Chabad 138
Basis of custom in ruling of Admur in Siddur: In Igros Kodesh ibid the Rebbe explains our custom is rooted in the wording of Admur in his Siddur as Admur states “One needs to recite the blessing first and then afterwards say the Yehi ratzon”. The words “first and afterwards” are seemingly superfluous. Hence one must learn it is coming to teach us that one is to say the Yehi Ratzon immediately after the blessing of Haeitz. Thus in conclusion Admur in the Siddur retracted his ruling from the Shulchan Aruch, and this is the source behind our custom. [Rebbe ibid]
The reason: The prohibition of making an interval between the blessing and eating is only a matter of Lechatchila in a case that the interval relates to the food. Now, since we Halachicly desire the Yehi Ratzon prayer to be recited as close as possible to the eating of the apple therefore in this case we allow even initially for one to say the Yehi Ratzon after the blessing, before the eating, as a time of need receives the same ruling as Bedieved. Now, regarding the reason why we desire the Yehi Ratzon prayer to be recited as close as possible to the eating of apple 1. See Sdei Chemed ibid who brings reasons according to Kabala for preceding the Yehi Ratzon to the eating 2. We desire the Yehi Ratzon to begin with a Bracha, similar to Tefilas Haderech [see 110/7] 3. We desire the Yehi Ratzon to be considered like a blessing in order to strengthen its power and effect. 4. A matter that is done for a good Omen must be grabbed at its first opportunity. Regarding why we do not precede the Yehi Ratzon to the blessing this is because a) It is similar to Leishev Bassukah that is not recited until after the blessing. [see 643] b) It is improper to precede the request of man to the praise of Hashem in the blessing. [Rebbe ibid; see Alef Hamagen 583/13]
Alternative reason: It is only an interval if one says the Yehi Ratzon with Hashem’s name, while if Hashem’s name is not said, as is our custom, then it is not an interval. [Nitzutzei Rebbe 10 brought in Hiskashrus 547]
 Siddur Admur [specifically writes “It is customary to eat the apple with honey on the first night”] Rav Hillel Paritcher in Pelach Harimon Vayeira p. 61:4 in name of Tzemach Tzedek [“This is the reason we are accustomed to eat the apple on the first night of Rosh Hashanah”]; Bnei Yissachar Tishrei 2/11 [not the custom even amongst the scholarly Rabbis, and not brought in any previous Poskim]; Ashel Avraham 583 [not the custom]; Darkei Chaim Veshalom 707; Alef Hamagen 583/18; Otzer Minhagei Chabad 150
 Sefer Haminhagim p. 118 records that there is a dispute involved as to whether the blessing over the apple exempts the fruits eaten for dessert and hence due to this the Previous Rebbe would specifically have in mind not to include other fruits that will be eaten for dessert, and he would recite a second blessing over them later on. However it is evident from many other sources that the previous Rebbe specifically had in mind to exempt the fruits eaten at the end of the meal. [Reshimos 4 p. 8 [so was the custom of the Rebbe Rayatz]; Sefer Hasichos 1945 p. 4 [that so was the custom in Lubavitch to have the dessert in mind] See Otzer Minhagei Chabad p. 79-80; Shulchan Menachem 3/85 footnote 3; Hiskashrus 947] Vetzaruch Iyun Gadol as what exactly is the dispute involved regarding the dessert? Perhaps one must conclude that the entire custom of the Rebbe Rayatz was based on the custom of Lubavitch to eat the apple before Hamotzi in which case there is discussion regarding the after blessing. See Koveitz Oholei Torah 640/15 for the source of the dispute.]
 This applies even if the fruit was not yet on the table, so long as it was already intended to be eaten during the meal. If however one did not have in mind the other fruits and it was then decided to eat it, after the Haeitz was already recited, then a new blessing of Haeitz is to be recited if there are no more fruits remaining on the table. [See Seder Birchas Hanehnin 9/5]
 Seder Birchas Hanehnin 9/16; Piskeiy Teshuvos 583/2
 Drashos Mahril R”H; Darkei Moshe 583/3; Elya Raba 583/3; Birkeiy Yosef 583/4 states that although the Rashbatz argues against this custom, nevertheless it does contain Kabalistic meaning.
 Ben Ish Chai Parshas Nitzavim 4
 Ben Ish Chai Parshas Nitzavim 4
 Ben Ish Chai Parshas Nitzavim 4
 Rav Hillel Paritcher in Pelach Harimon Vayeira p. 61:4 in name of Tzemach Tzedek
 Shir Hashirim 2
 All fruit trees are rooted in one of the Middos and the Middos in turn receive from the level of shade, which is a contracted form of Keser.
 Torah Or Shemos in Hosafos
 Yifei Laleiv 3/1; Kaf Hachaim 583/17; Torah Or Shemos in Hosafos