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The Gemara (Menachos 36b) writes:

אמר ר' אלעזר כל המניח תפילין אחר שקיעת החמה עובר בעשה ור' יוחנן אמר עובר בלאו

R’ Elazar said: whoever places Tefillin after sunset violates a positive commandment. And R’ Yochanan said: he is in violation of a negative commandment.

The Halacha follows R’ Yochanan (Rambam, Hil. Tefillin 4:10-11).

Why should he be in violation already from sunset?

Since it’s a doubt whether it’s day or night between sunset and Tzeis, there seems to be two conflicting mitzvos here: the mitzvah to place Tefillin by day, and since we’re stringent by a doubt of Torah law, one should wear them; and the mitzvah not to place Tefillin by night, and since we’re stringent by a doubt of Torah law, one should not wear them.

But there’s a concept called אתי עשה ודחי לא תעשה, that when a positive commandment and a negative commandment are in conflict, one should do the positive (see further here). Why don’t we extend this principle to here, and one should potentially fulfill the mitzvah after sunset, against the potential prohibition of wearing them at night? Why doesn’t a doubtful positive commandment override a doubtful negative commandment, the same way that a certain positive commandment overrides a certain negative commandment?

DonielF
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    Why do you think it's a doubt after sunset just because it's doubtfully daytime? It's not like the obligation starts at dawn when the daytime starts. Tefillin isn't obligatory for the whole daytime. (It's not obvious as well BTW that the Rambam thinks it's actually Safek night after Shkiya.) – Double AA Nov 22 '18 at 16:15
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    The positive and negative commandments aren't in contradiction here at all. We just don't know which is in play. I don't see why Aseh Doche Lo Taaseh would apply. – Double AA Nov 22 '18 at 16:18
  • It's referring to someone who wraps tefillin davka after shkia l'chatchila(and not during the day, possibly). B'diavad, even the Rambam holds it's permitted(and probably obligatory for someone who didn't wrap during the day). – chacham Nisan Nov 23 '18 at 06:35
  • @DoubleAA Where in the Rambam do you see that he might not hold Bein HaShemashos is a safek? I assume that if Tefillin is a Mitzvah of the day, it applies all day - therefore there’s a doubt whether the positive applies Bein HaShemashos, or whether the negative one does. – DonielF Nov 23 '18 at 12:25
  • @chachamNisan Do you mean bediavad in its actual sense, that once one has done it it’s okay? No. It’s not okay in this case. Otherwise, why would one be in violation of anything? I can edit in a different part of the Rambam where he contrasts this to one who put on Tefillin before Shekiah and left it on, where it’s fine, but we try to avoid it, if that helps make the line clearer. But i think the Gemara is perfectly clear - whoever places it after Shekiah violates a lav. – DonielF Nov 23 '18 at 12:30
  • @Doniel We've already established Tefillin is not a Mitzva of the day that it should apply all day. It doesn't apply when the day starts at dawn all the way until Misheyakir. So it doesn't apply all day. Your assumption isn't applicable. ||| I didn't say the Rambam doesn't think Bein Hashemashot isn't Safek. He just might not think BhSh starts right after sunset. (The Talmud too for that matter.) – Double AA Nov 23 '18 at 13:13
  • The Gemara states that it's permitted to wear them after shkia(and even nighttime) in order to protect them. Not only that, but Rav Ashi states that nighttime is zman tefilin(even though we don't moreh halacha like that). If it really was a lav, how could the Talmud and Rav Ashi permit wearing tefilin after shkia and nighttime? Also, it could be that he was over the lav because he wasn't shomer(careful) with the mitzvah of tefillin by waiting until shkia; not that there's an issur to wear them then. Further support is the conclusion of the talmud that it's still – chacham Nisan Nov 24 '18 at 18:42
  • day until two medium-sized stars appear in the sky(the actual time for bein hashemashot and thus safek yom/safek laila; see Shabbat 35b and the statements of Rabi Yehuda and Shmuel regarding bein hashemashot). – chacham Nisan Nov 24 '18 at 18:45

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