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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?

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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 6:35
  • @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

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