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Dipping the Challah in honey:
There are those that are accustomed to dip the piece of Challah from Hamotzi into honey. [This is an ancient Ashkenazi custom and is the practical Chabad custom followed today. Today this custom is also followed by segments of Sefaradi Jewry.]
When? The Challah is dipped in honey throughout all the meals of Rosh Hashanah, both by night and day. Furthermore, it is customary to dip the Hamotzi bread in honey throughout all the Yom Tov [i.e. two days of Sukkos] and Shabbos meals until Hoshanah Raba. It is likewise dipped in honey on Hoshanah Raba and Erev and Motzei Yom Kippur. During the other weekdays however it is not customary to do so. On Shemini Atzeres and Simchas Torah one does not dip the bread of Hamotzi in honey. During Chol Hamoed Sukkos, including Shabbos Chol Hamoed, it is not our custom to dip the Challah in the honey.
How many times is one to dip the Challah into the honey?
The Rebbe was accustomed to dip the Challah into the honey three times.
Does one also dip the Challah in salt? Is one to also have salt on the table?
Some Poskim rule one is to dip the Challah in salt three times, and only afterwards dip it in honey. [In certain years the Rebbe dipped the first piece three times in honey and then a second piece three times in salt. During the Rosh Hashanah Farbrengens the Rebbe was witnessed to dip the first piece in honey and the second piece in salt. Practically the current widespread Chabad custom is to only dip the Challah in honey, although nevertheless one also makes sure to have salt on the table.]
During the Rosh Hashanah meals, after saying the blessing of Hamotzi, one dips the Challah in the honey [three times]. Nevertheless one should also have salt on the table. It is customary to dip bread in honey throughout all the Yom Tov and Shabbos meals until Simchas Torah, as well as Hoshanah Raba, Erev and Motzei Yom Kippur. During the week it is not customary to do so.
The ancient custom of Ashkenazi Jewry is to eat round Challahs on Rosh Hashanah. This symbolizes the roundness of a crown and corresponds to the coronation of Hashem on Rosh Hashanah. Alternatively it is done as a symbol of good omen as all round items do not have a start or finish and hence reflects long life. Likewise round represents unity. Some write that this applies only on Rosh Hashanah itself, however on Shabbos Shuva one is to return to the accustomed shape of the two Vav’s.
 The reason: This is done as an omen that the new year will be sweet and good upon us. [Levush 583/2]
Sugar: The Kaf Hachaim 582/4 mentions sugar as an alternative to honey.
Yehi Ratzon: It is not our custom to recite the Yehi Ratzon after dipping the Challah in honey. [Sefer Haminhagim p. 118-English; Alef Hamagen 583/8] However some are accustomed to recite the Yehi Ratzon after dipping the Challah in honey and then again after dipping the apple in honey. [Mateh Efraim 583/1; Taamei Haminhagim p. 310]
 Levush 583/2
 See Sefer Haminhagim p. 145 [English]; Mamarim Haketzarim of Admur Hazakein p. 454 has a Mamar titled “To understand the concept of dipping Hamotzi in honey from Rosh Hashanah until after Hoshanah Raba”; See Otzer Minhagei Chabad 130
 Kaf Hachaim 583/4
 Kaf Hachaim 583/4
 Sefer Haminhagim p. 145 [English]; Likkutei Sichos 14 p. 372; Hayom Yom Vol. 2 [See Otzer Minhagei Chabad Sukkos 136 that the Rebbe was witnessed on Sukkos to dip the Challah three times in salt at the end of the meal.]
 Likkutei Sichos 14 p. 372; omitted from Sefer Haminhagim ibid and Hayom Yom ibid
 Mamarim Haketzarim ibid “Until after Hoshanah Raba”
Other customs: Darkei Chaim Veshalom 707 records until Shemini Atzeres, including Shemini Atzeres, and so is written in Ketzei Hamateh 605/38 and Piskeiy Teshuvos ibid. Some are accustomed to do so until Shabbos Bereishis. [Minhag Chassidim recorded in Piskeiy Teshuvos 583 footnote18]
 Sefer Haminhagim p. 145 [English]; Hayom Yom Vol. 2
 Likkutei Sichos 14 p. 372; Hayom Yom vol. 2
 Ketzei Hamateh 605/38; Piskeiy Teshuvos 583/3 footnote 19; In Likkutei Sichos 14 p. 372 the Rebbe writes “it requires further analysis if this refers to only the meals of Shabbos and Yom Tov or even the meals of the week.” however in Hayom Yom [2nd year] the Rebbe lists clearly all the days that Challah is dipped in honey, and the weekday is not listed. See Otzer ibid 135
Other Customs: Some are accustomed to dip the Challah in honey even during the weekday meals. [See Piskeiy Teshuvos ibid]
 Sefer Haminhagim p. 147 [English] based on Mamarim Haketzarim ibid
 Sefer Haminhagim p. 145 [English]; Hayom Yom 2nd year; Sefer Hasichos 1944 p. 24; [The Rebbe writes that there is no reason to require dipping in honey during Chol Hamoed, including Shabbos Cho Hamoed. [The English translation in Sefer Haminhagim ibid writes that this matter is optional, it is however clear from the Rebbe’s wording in Hayom Yom as well as the original words in Sefer Haminhagim in Hebrew that this is not our custom, and is not merely optional. See Otzer Minhagei Chabad Sukkos 136] However see Otzer ibid that the Rebbe was once seen to dip the Challah in honey during the Farbrengen of Chol Hamoed Sukkos.
Other Customs: Some are accustomed to dip the Challah in honey even during Chol Hamoed. [See Piskeiy Teshuvos 583 footnote 19]
 Otzer Minhagei Chabad 131; Hiskashrus 947
 Kaf Hachaim 583/4 [“First one is to dip it in salt and afterwards he is to dip it in honey.”]; Piskeiy Teshuvos 583/3 [some dip one side in honey and one side in salt]; Rav Hillel Paritcher is recorded to have first dipped the Challah in salt and then eat a Kezayis, and only afterwards did he dip it in honey. [Otzer Minhagei Chabad 132] This custom is also recorded in Taamei Haminhagim p. 310 and Piskeiy Teshuvos ibid]; See Otzer ibid 134 for custom of other Chassidic groups.
The reason: “One is not to dip it in honey without salt as salt is required to sweeten the severities and hence based on Kabala is never to be nullified.” [Kaf Hachaim ibid; Otzer ibid in name of Hillel Paritcher]
 Otzer Minhagei Chabad 131; This custom to dip first in honey and then in salt is also recorded in Salmas Chaim 1/346 and Piskeiy Teshuvos ibid.
 Hiskashrus 897
 Shevach Hamoadim 7/5; Hiskashrus 897; see Otzer Minhagei Chabad 133 who infers from Sefer Hasichos 1939 p. 304 that the custom was not to even leave salt on the table.
 Piskeiy Teshuvos 583 footnote 46; 242 footnote 105; Otzer Minhagei Chabad 129
 Brought in Piskeiy Teshuvos 583 footnote 46