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Beit Midrash
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Answer: Let us start by citing cases of tvlmh found in Shas. If one "forms" a sukka by hollowing out a pile in a way that leaves sukka-kosher objects over the space, the sukka is pasul until moving the s’chach. One needs to positively place s’chach over an area (Sukka 12a). If the tzitzit of a garment are attached before it is obligated in tzitzit, the tzitzit must be reattached (Menachot 40b). Mezuzot must be placed on an obligated doorpost and not placed on a board which later helps form such a doorpost (ibid. 33b). The gemara raises the possibility that tvlmh applies to hadasim connected to a lulav when they were invalid and remain after they were fixed (Sukka 33b).
There are some grounds to compare our case to the Talmudic cases. We will see if there are distinctions that would justify the apparent practice that people do not refasten the tefillin after removing the sleeve. First, we note that the gemara and Rishonim do not discuss tvlmh in regard to tefillin. Some say (see discussions in Levushei Mordechai, Yoreh Deah II:122 and Shevet Halevi II:154) that tvlmh applies specifically to mitzvot for which the Torah uses the root aso (do/make), i.e., sukka and tzitzit. Some explain that mezuza is only Rabbinical (opinion in Sdei Chemed, vol. V, p. 330) or a loose use of the term (Levushei Mordechai ibid.); lulav is unclear and might be because of its connection to sukka. This might (see later) remove the whole question.
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The Shevet Halevi (ibid.) points out that the classic tvlmh sources refer to preparing various mitzva objects (sukka, garment with tzitzit), not to the performance of the mitzva. One could use that distinction to negate any problem of tvlmh regarding fastening, but he argues that the need for direct action regarding the actual fulfillment of the mitzva is broader than the issue of tvlmh. However, the Shevet Halevi posits that just like when tvlmh disqualifies s’chach, this is remedied by shaking the s’chach (Sukka 15a), removing the chatzitza to fix the tefillin’s position is positive "doing." The Eshel Avraham (Butchach), 27:4 said this before him.
Other opinions lend room for leniency. The Rashba (Megilla 24b) says that a sleeve under tefillin shel yad is not a matter of chatzitza; rather, tefillin should be under a covering rather than on top of it because it is "a sign for you" (Shemot 13:9). Therefore, says Rav Frank (ibid.), the fastening was not intrinsically flawed, and when the "side problem" is solved, one does not need a new action. A precedent for this concept is the Rama (OC 626:2) – a sukka under a pasul overhang becomes kosher when the overhang is removed without further action because external problems do not create tvlmh problems.
Also, perhaps a chatzitza on a minority of the place of the tefillin does not disqualify (Eshel Avraham ibid. considers it a possibility). If that opinion is correct (although we do not rely upon it l’chatchila), the whole question disappears. Perhaps even if one does not fulfill the mitzva with a partial chatzitza, fastening it in that way is at least considered a mitzva action.
Because there are so many possible reasons for leniency, and several of them are strong reasons that negate the problem, there is no need in practice to refasten the tefillin shel yad after the sleeve is rolled back.
Bemare Habazak - Rabbis Questions Ask the Rabbi: Using Replacement Mezuzot When They Are Being Checked?
Rabbis in Midrash
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