Should a person recite the Beracha of "Shehehiyanu" the first time he wears Tefillin, just as we recite "Shehehiyanu" when we perform annual Misvot, such as Lulab, Sukka and Shofar?
The Tosefta in Masechet Berachot (chapter 6) states explicitly that one recites "Shehehiyanu" when wearing Tefillin for the first time, just as one recites the Beracha the first time he takes the Lulab each year on Sukkot (listen to audio recording for precise citation). This is, indeed, the ruling of the Sefer Ha’roke’ah (Rabbi Eliezer of Worms, 1165-1240), in Siman 371, that one recites "Shehehiyanu" when wearing Tefillin for the first time, based on this passage in the Tosefta. This was also the position taken by the Radbaz (Rabbi David Ben Zimra, Egypt, 1479-1573), in his responsa (Siman 5), where he notes that new Tefillin are no different than new garments, upon which one recites the Beracha of "Shehehiyanu." Many other Halachic authorities also followed this ruling.
By contrast, Tosafot (Talmud commentaries by Medieval French and German scholars), in Masechet Menahot (75), maintain that "Shehehiyanu" is recited only on Misvot that are observed on rare occasions. Tefillin is a Misva that we perform virtually every day (the exceptions being only Shabbat and holidays), and according to Tosafot, the Beracha of "Shehehiyanu" is not recited over Misvot of this sort. The Beracha is recited over Misvot like Shofar and Sukka, which we observe on rare occasions, but not on a Misva like Tefillin, even the first time it is observed.
Others challenged Tosafot’s line of reasoning, noting that wearing Tefillin for the first time in one’s life is no less significant an event than performing an annual Misva like Shofar and Lulab. Even though the Misva of Tefillin is observed every day, the joy experienced the first time it is observed should be at least equivalent to the joy of performing a yearly Misva, and should therefore warrant the recitation of "Shehehiyanu." This argument was raised by the Petah Ha’debir (Rabbi Haim Binyamin Pontrimoli, Turkey, 19th century; listen to audio recording for precise citation), who also noted the counterargument, that one may, indeed, distinguish between wearing Tefillin for the first time and performing an annual Misva. We might say that the Beracha of "Shehehiyanu" was not instituted over an everyday Misva like Tefillin, even the first time it is performed, because even if the person had himself never before performed the Misva, everyone else around him has. Misvot like Shofar and Lulab are inherently restricted to a certain period, and do not apply to anybody at other times, and thus the occasion of performing those Misvot warrants the recitation of "Shehehiyanu." When it comes to Tefillin, however, since the Misva is generally observed everyday, it is not recited even when one wears Tefillin for the first time in his life.
As for the final Halacha, the Hid"a (Rav Haim Yosef David Azulai, 1724-1806), in his Mahazik Beracha (22), writes that the accepted custom follows Tosafot’s view, that "Shehehiyanu" is not recited the first time one wears Tefillin. Similarly, the Damesek Eliezer writes that he never saw anyone observe such a practice. This is also the ruling of the Kaf Ha’haim Palachi (10:8), and appears to be the view of the Shulhan Aruch (Orah Haim 22).
Summary: One does not recite the Beracha of "Shehehiyanu" on the occasion of wearing Tefillin for the first time.
