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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.
Bemare Habazak - Rabbis Questions (654)
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408 - Consequence of Removal of Sleeve from under Tefillin
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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.
Kuzari -Rabbi Ari Shvat Kuzari class 8- "Answering Questions on the Kuzari's Proof from Mass Revelation
Rabbis in Midrash
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Kuzari -Rabbi Ari Shvat Kuzari class 9 - "Seeing is Believing" (parag. 21-30)
These paragraphs elaborate on the theme that seeing and knowing is better than any attempt to prove logically, and begins explaining the difference between Israel and gentiles.
Ein Aya Various Universal Stages of the Geula Process
Rav Kook examines the various stages of redemption, explaining how (in addition to the obvious oft-mentioned stages of ingathering the exiles, reviving the Hebrew language, army, state etc.) the messianic dream of world prosperity, the State of Israel and world unity can and are realistically and logically gradually coming true.
Kuzari -Rabbi Ari Shvat Kuzari class 8- "Answering Questions on the Kuzari's Proof from Mass Revelation
How do we know that the "claim" of mass revelation to 2,000,000 witnesses at Mt. Sinai is really true? This important class answers all of the questions skeptics ask about this claim of the Kuzari.
Ein Aya Armies Still Necessary for Balance & the War Against Wars
Rav Kook explains why the world was originally divided into the various seemingly contradicting ideologies and cultures, in order to develop each one respectively. Swords or armies symbolize how each respective ideology defends themselves, as well as deters their opposing ideologies and cultures. On the other hand, the messianic era will be one of peace, and Rav Kook explains the transition to that stage, which mankind is already undergoing.
The Land of Israel LGBT'S IN ISRAEL
The question was asked, how can one make Aliyah with the LGBT parades?
Kuzari -Rabbi Ari Shvat Kuzari class 7 - Five Accumulative Proofs of G-d
As a preparation for the Kuzari's classic proof of G-d from the mass-revelation at Sinai, we start here with 5 other directions to strengthen our belief which also contribute to what the Kuzari will present as well.
Ein Aya Muscle & Meaning: The Dual Nature of Gevurah (Physical Strength)
Is physical strength and fitness a necessity or an ideal? Although it if often totally overlooked among topics of Judaism, Rav Kook writes that it clearly is also a necessity to deter the many enemies of Israel, but even in Y'mot HaMashiach, in the Messianic era, to a certain extent, it's ideal continues even after our enemies will have been finished off.
