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The decree of keeping two days of Yom Tov outside of Israel is because Rosh Chodesh used to be determined by Beis Din and its messengers couldn't reach all of exiles in time, thereby requiring people living outside the range to keep two days out of doubt. Therefore, nowadays we keep two days like out forefathers did.

My question is, why do we not put on tfillin on the second day of yom-tov (Rosh Hashana, Simchas Torah, 8th day of Pesach) out of sofek?

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  • That is indeed the normative practice of an Israeli who finds himself in Exile for a yom tov. He cannot do melacha on day two or eight, since it is the custom of those around him not to. However, he does put on tefillin on day eight of pesach / sukkos, and day two of shavuos, because "safek d'oraisa l'chumra". However, one must be careful to do this privately, and not violate "al tifrosh min ha tzibbur".
    – user1095
    Jan 31, 2012 at 7:21
  • Also, such a person would pray the weekday prayers, again, in private.
    – user1095
    Jan 31, 2012 at 7:22

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Today we don't treat the second day of yomtov as a "maybe it's yomtov"; it has been rabbinically enacted for us (non-Israel-dwellers) as a full-fledged yomtov.

The Talmud established long, long ago that rabbinic law has the power to order someone to be passive rather than fulfill a Torah obligation, e.g. not putting on tefilin on 2nd day yomtov (or not blowing Shofar if Rosh HaShanah is on shabbos).

I see your question is "the custom is done the way it was done then." Actually no; back then, a visitor to Israel would keep one day. While Rabbi Emden insists that should be the case today as well, Rabbi Feinstein says that when the practice was fixed its parameters changed; now you follow your hometown instead. Similarly, Ritva says that today, the borders of Israel with regards to 2nd day yomtov are the Biblical ones, even though back then it all had to do with where they could send messengers (much closer to the Talmudic borders).

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  • @tomsmith this answer may help your understanding. Essentially, it is a custom today.
    – yydl
    Oct 4, 2011 at 3:57
  • it may have even been enacted that way then, or perhaps it was enacted later. note that R.H.Schachter holds a visitor to Israel should do that on the second day.
    – Ariel K
    Oct 4, 2011 at 4:19
  • so if it was just a sefek for regular yom tov sheni, R.HS would hold you should put on tefillin then, so it must be some sort of gzeira.
    – Ariel K
    Oct 4, 2011 at 14:05
  • if RHS held like r'emden fully, he should definitely hold one should daven like on a weekday, even if he still doesn't do melacha.
    – Ariel K
    Oct 4, 2011 at 14:06
  • Rabbi Yaakov Emden says follow the Israelis completely. Put on tefillin and go to work.
    – Shalom
    Oct 4, 2011 at 16:00

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