The order in removing the Tefillin:

Which is removed first-Shel Yad or Shel Rosh?^[1] When one removes the Tefillin, the head Tefillin must be removed prior to the hand Tefillin.^[2]

Removing the straps of the Shel Yad:^[3] Some^[4] are accustomed for reasons known to them to remove the head Tefillin before removing any of the straps of the hand Tefillin from one’s finger. Others^[5] are accustomed for reasons known to them to remove the [three^[6]] straps [of the finger] prior to removing the head Tefillin.^[7] [Furthermore, some are accustomed to remove up to 2-3 straps from the arm, and only then remove the head Tefillin.^[8] Practically, the widespread custom today is to first unwrap the straps of the fingers [and not the arm], and only then to remove the Shel Rosh.^[9] The Rebbe Rashab would remove several straps also from the arm, thus loosening the attachment of the Shel Yad to the biceps, prior to removing the head Tefillin.^[10] Many within Chabad would follow this custom.^[11] The Rebbe however expressed that he did not have knowledge of this custom, and seemingly only removed the straps from his fingers, and not from his arm.^[12]]

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[1] Admur 28/3; Michaber 28/2; Menachos 36b

[2] The reason: As if one first removes the Shel Yad, it is found that he is left wearing only the Tefillin Shel Rosh, and the Torah said “Vehayu Letotafos Bein Einecha”, and the Sages expounded that so long as the Tefillin are between your eyes, you should be wearing both Tefillin. It is for this reason that the verse states “Vehayu” which is in plural tense, and does not simply state “Ukeshartem Leos Al Yadecha Uletotafos..” [Admur ibid; Michaber ibid; Menachos ibid]

[3] Admur 28/6

[4] 1^st opinion in Admur ibid; M”A 28/2 in name of Galya Raza as brought in the Nussach of Beir Heiytiv and P”M 28 A”A 2

[5] 2^nd opinion in Admur ibid; M”A 28/2 in name of Galya Raza as brought in our Nussach; Elya Raba 28/4, brought in P”M ibid, in name of Galya Raza; Yifei Laleiv 28/3; Shaareiy Teshuvah 25/15 in name of Hagahos of Rav Shmuel Vital in Shaar Hakavanos Derushei Tefillin Derush 5

[6] P”M 28 A”A 2; M”B 28/5; Likkutei Maharich Seder Mitzvahs Tefillin in name of Mishnas Chassdim; Siddur Rav Shabsi; Or Tzadikim

[7] The reason: Perhaps the reason for this is because in truth one should remove the Shel Yad before the Shel Rosh, as it was the first that was worn, and doing so respects the Shel Rosh who will remain longer on the head. However, since the Shel Rosh cannot be on without the Shel Yad, therefore we only remove a few straps of the Shel Yad. [Ishkavta Derebbe footnote 25]

[8] Shaariey Teshuvah 25/19 in name of Hagahos of Rav Shmuel Vital ibid “Prior to removing the Shel Rosh, one is to remove the straps from the finger, and 2-3 straps from the arm.”; Machazik Bracha 25/10 and 28/4; Shalmei Tzibur p. 42; Zechor Leavraham 1 Taf; Kitzur Shelah; Nivei Shalom 28/6; Chesed Lealafim 28/3; Kaf Hachaim [Falagi] 10/40; Ben Ish Chaiy Chayeh Sara 9; Kitzur SHU”A 10/20; Artzos Hachaim 28/6; See Kaf Hachaim 28/5

The reason: Perhaps the reason for this is because in truth one should remove the Shel Yad before the Shel Rosh, as it was the first that was worn, and doing so respects the Shel Rosh who will remain longer on the head. However, since the Shel Rosh cannot be on without the Shel Yad, therefore we only remove a few straps of the Shel Yad. However, one should remove up until a few straps from the arm in order to loosen  the grip of the Shel Yad to the arm and hence make it considered as if he already removed the Shel Yad Tefillin. [Ishkavta Derebbe footnote 25]

[9] P”M 28 A”A 2; Misgeres Hashulchan 10/15; Likkutei Maharich Seder Mitzvahs Tefillin; Ketzos Hashulchan 8/17; See Ishkavta Derebbe p. 42 footnote 25

[10] Ishkavta Derebbe footnote 25

[11] See letter in Shulchan Menachem 1/86 “You mention in your letter that our custom is to remove a number of straps of the arm prior to removing the Shel Rosh.”

[12] See letter ibid that “Certainly you have seen or heard this from somewhere, and let me know in detail, because I have not heard this.” In a reply from Rabbi Leibal Groner, he stated that he did not pay attention to the Rebbe’s practice regarding this issue