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There is a fundamental Machlokes Rishonim whether when the Gemara says that there is no Chiyuv of Tzitzis at night, is that referring to the Gavra or to the Cheftza. The question now is: a person puts on Tzitzis for the first time during Bein Hashmashos (or he puts on again, according to many Acharonim), does he make a Bracha? It seems like it should be a Sfek Sfeika about whether he should not make a Bracha, and therefore he should. However, the Sfeikos regarding Bein Hashmashos and Brachos are very complicated. Thank you so much in advance.

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    You can practically also add another safek that maybe bein hashemashot doesn't really start yet when you normally think it does. But your question alone is interesting in the hypothetical that you know when for sure bein hashemashot is. – Double AA Jul 6 at 0:33
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    The Mishnah berurah elsewhere brings achronim who say not to make a bracha even if you have a sfek sfeika telling you to. However, there seem to be cases which that rule is ignored for some reason, and the meforshim are busy trying to answer the contradiction – robev Jul 6 at 1:54
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Mishnah Berurah 18:7

אבל אם איחר להתעטף עד לילה שוב לא יברך דשמא הלכה כהרמב"ם ומשמע מדברי המ"א בסק"ד דאפילו בין השמשות מותר לברך עד צה"כ וטעמו דהלא בציצית לא כתיב יום רק וראיתם אותו משמע כל זמן שנוכל לראות וכן פסק בעל דרך החיים ובספר מטה אפרים ראיתי שמחמיר בזה אך אם זה גופא הוא מסתפק אם כבר הגיע בין השמשות נראה דבודאי יוכל לברך דבלא"ה דעת התוספות והרא"ש דכסות יום חייב בלילה והגר"א בביאוריו מצדד ג"כ לשיטה זו עי"ש

But if he delayed wrapping [himself with tzitzit] until night he should no longer make a blessing, for maybe the law accords with the Rambam. And it is implied from the words of the Magen Avraham in Subparagraph 4 that even [during] bein hashemashot it is permissible to make a blessing until tzeit hakochavim. And his reason is that by tzitzit [the verse] does not say "day"; it just says "and see it", [which] implies that any time that we are able to see it. And so rules the author of Derech Hachaim. And in the book Mateh Ephraim I saw that he is stringent about this. However, if this itself he is unsure of [i.e.] whether it is already bein hashemashot, it would seem that he can certainly make a blessing, for in any case the opinion of Tosafot and the Rosh is that a day garment requires [tzitzit] at night. And the Gra in his commentary comes out as well towards this view, see there.

Aruch Hashulchan O.C. 18:9

אך לאחר שקיעת החמה נראה שאין לברך עליו

But after sunset it would seem that he should not make a blessing on it.

You're suggested sfeik sfeika is actually mentioned by R. Akiva Eiger (O.C. 18), but he doesn't seem sure about it. Commenting on the Magen Avraham's statement that you can make a blessing until tzeit hakochavim, R. Eiger writes:

ק"ל הא שאני דעמוד השחר הוא יום מדינא משא"כ בבה"ש הוי ספק לילה ואיך יברך מספק ואפשר דהוו ס"ס ס' יום ב' וספק דכסות יום חייב בלילה וצ"ע לדינא

This is difficult to me, for amud hashachar is different since it is day by law, whereas bein hashemashot is possibly night, so how can one make a blessing from doubt? And it it possibly a sfeik sfeika: 1) It is possibly [still] day 2)Perhaps a day garment is obligated [in tzitzit even] at night. And this requires analysis for the [final] law.

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