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I've read this M.Y. question that explains why tefillin are removed before Musaf on Rosh Hodesh and Hol Hamo'ed.

From what I have noticed in Nusach Ashkenaz shuls, on Hol Hamo'ed Pesach, tefillin is removed before Hallel whereas on Rosh Hodesh, they are kept on for Hallel and removed prior to Musaf. Why is there a difference?

Note: I intentionally did not ask about Hol Hamo'ed Succot, because I have heard that the wearing of tefillin is considered chatzitza when you are holding the arbah minim (four species) during Hallel. Thus, the tefillin are removed prior to Hallel.

  • When it comes to when and if to take off Tefillin on Chol HaMoed and Rosh Chodesh, every opinion possible exists. – Double AA May 15 '19 at 21:18
  • @DoubleAA Doesn't surprise me. I would hope that at least most of them have some reason behind it other than, "I'm following everyone else." – DanF May 15 '19 at 21:32
  • The minhag I've seen is that on Chol Hamoed, the tefillin are removed before Hallel. The exception to this minhag is the first day of Chol Hamoed Pesach, when the kriah is the first two parshiyos of tefillin, when the tefillin are removed before Mussaf. – Menachem May 15 '19 at 21:46
  • @Menachem I have heard and read about the exception for 1st day HHP since the Torah reading mentions tefillin. I haven't been in any shul that follows this minhag, though. – DanF May 15 '19 at 21:48
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There is no dispute that ראש חדש is definitely a day which has an obligation to don תפלין. (Why we actually remove them before מוסף is a separate discussion.) The רמ"א in OC 25:13 also mentions that one should preferably hear 3 קדודות and 4 קדשים, which is not accomplished until the קדיש preceeding מוסף.

On חול המועד, since there is a disagreement according to the פוסקים, most people only don תפלין for the bare minimum. The רמ"א (ibid) actually seems to indicate that there is no difference between ר"ח and חוה"מ.

Since the רמ"א makes no distinction with regard to סכות vs. פסח, it would seem that there is no חציצה problem with the אתרוג. Either it is not a problem at all because we are doing a מצוה, or it there is no actual חציצה since the fingertips are never covered.

As an aside, I can testify that in KAJ in New York, there is a distinction between פסח and סכות with regard to the חזן. On פסח, where there is no break to pick up the ארבע מינים before הלל, the ש"ץ (who cannot remove תפלין after קדושה) does not remove תפלין until שיר של יום (which is recited before קריאת התורה) to avoid טירחא דצבורא.

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