I revisited this topic later - see here
At the Shacharis (morning) service of Rosh Chodesh, we take a seemingly out-of-place pause to take off our tefillin (see also here) before reciting the Mussaf service.
Normally, on days they are worn, the tefillin are left on until the end of the service. Why are they taken off early on a day when Mussaf is recited, such as Rosh Chodesh, and Chol Hamoed? [Most people who wear tefillin on Chol Hamoed take them off before Hallel.]
It seems there are a few reasons:
The main reason is recorded by Yosef Caro in his "Beis Yosef" (Tur O”C 25) (see also here for his biography). He says the reason for removing tefillin before Mussaf on Rosh Chodesh is because it is our custom to say the kedusha prayer of “Keter yitnu l’kha” – that God will be given a crown by the angels - and it is inappropriate for us to be wearing a crown (tefillin) when talking about God's crown.
Following this line of thinking, the Rama (Rabbi Moshe Isserlis) says the custom to take the tefillin off before Mussaf should only apply in a synagogue where the "Keter" kedusha is recited, ie. in a Nusach Sfard minyan. [The Ashkenazic community has a different kedusha which does not mention a crown.] However, the custom to remove the tefillin has become widespread and it is the practice everywhere.
Another reason for taking off the tefillin, even when not saying the kedusha of “keter” is because the recitation of Mussaf is akin to bringing sacrificial offerings, which remind us of holiday celebrations. Once we are reciting Mussaf, the day is like a holiday and tefillin are not worn . (Taamei Haminhagim)
When are they to be taken off?
Magen Avraham (Rabbi Avraham Gombiner) (s”k 30) says they are taken off after the Torah is returned to the Ark (he is assuming it is returned after Uva L’Zion, right before Mussaf, as is done on Shabbos and Yom Tov), which rejects the opinion of the L’vush to take the tefillin off before Torah reading. Magen Avraham's reason – it is merely a custom to remove them on Rosh Chodesh before Mussaf, but by no means a halakha (law), so it should be done as late as possible in the davening - but before Mussaf is actually recited.
Mishneh Brurah (s”k 59) records two opinions as to when to remove the tefillin.
a. Since in Ashkenazic synagogues the Torah is returned to the Ark right after the Torah reading (and not after Uva L’tzion or immediately before Mussaf is recited), the custom is to wait until after the kaddish before Mussaf, and then to remove the tefillin.
b. Eliyahu Rabba suggests the tefillin be removed towards the end of Uva L’tzion, but before the kaddish is recited, so as to avoid a hefsek (break) between kaddish and Mussaf.
Shaarei Teshuva (s”k 22) has a fascinating analysis over whether one needs to remove the tefillin at all, particularly in a rushed situation where there isn’t time to take them off. One might be able to move them to the side – off-center on the head – which is considered as if you’re not wearing them. If a person already prayed and put the tefillin back on for studying purposes or the like, and a second minyan is now praying, he need not remove the tefillin during kedusha, even if he says kedusha along with the later minyan. (Orchos Chaim says to cover the tefillin so they won't be visible.) He concludes quoting the Dvar Shmuel who mentions a custom not to remove the tefillin at all during Mussaf, neither on Rosh Chodesh or Chol Hamoed.
Point to Ponder
Mishneh Brurah (s”k 61) raises an interesting point. If the reason for removing the tefillin is to avoid saying “Keter” with tefillin on, then we should be removing the tefillin after the Silent Amidah in anticipation of when we’ll be saying kedusha, not before the silent Amidah. Nonetheless we remove the tefillin even for the silent Amidah. However, if a person forgot to remove the tefillin and is already praying the Mussaf Amidah, he need not pause to take off the tefillin, because taking off the tefillin for Mussaf is only a custom.
The Taz (s”k 16) quotes the Zohar (Kabbalistic work) who says wearing tefillin while saying “keter” is dangerous. There are, nonetheless, two schools of thought:
A. Those who without hesitation took the tefillin off, and
B. He mentions a “certain sage” who would not take his tefillin off for Mussaf, because it was not his custom to say “keter” in kedusha, and he justified his behavior saying he was not destroying a "minhag" because he can rely on the opinion that tefillin may remain on the person’s head.
– ps. Taamei Haminhagim concludes quoting the Zohar in Parshas Pinchas “Someone who prays Mussaf with tefillin on is worthy of death [“chayav mitah” – חייב מיתה]." I don't know what that means, but if taking off the tefillin is all I need to do to avoid such a culpability, I am happy to remove the tefillin before saying Mussaf.
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