Why did Yosef instruct the man to place his silver goblet inside the sack of Binyamin; would this not pain Binyamin more than the others?
Seforno: To see to what extent they were prepared to go to save Binyamin from slavery. 1 Ohr ha'Chayim (to 44:1) - This would atone for not acting with brotherhood towards Yosef.
Moshav Zekenim (to 44:12): This was to test if he is really Binyamin, or a waif. All would return with him only if he was truly their brother. 2
Yosef did not recognize him, for Binyamin was about nine when he last saw him. Even according to the Midrash that Yosef was moved to tears upon hearing that he named his 10 sons after him (refer to 43:30:1:1 and the note there), perhaps he was an imposter (for Yaakov would not let Binyamin go), and Binyamin told him to say so! However, even if he was a son of [e.g.] Reuven, who would be able to answer most questions about the family, the brothers would return to save him! (PF)
Why does the Torah add the words, "ki'Devar Yosef Asher Diber"? Above (42:25), it says only "va'Ya'as Lahem Ken"!
Ha'amek Davar #1: It was hard to fill the sacks to capacity.
Ha'amek Davar #2, Oznayim la'Torah: The man did not know the reason behind Yosef's instructions [to frame Binyamin]. Yosef had to decree that he not transgress his words, lest it be difficult for him to carry it out.
Why did Yosef scheme to frame the brothers for theft?
Ohr ha'Chayim #1: It was to atone for their having sold him. They would be shamed for a similar matter. Also refer to 44:2:1:1.
Ohr ha'Chayim #2: It was to hint to them that someone in this house recognizes their deeds. 1 We find that he hinted this to them in many ways, e.g. the way he seated them. 2
Thinking that someone knows their bad deeds would shame them and help them do a better Teshuvah (you should fear Hashem like you fear people, lest they know your deeds! - Berachos 28b). Aderes Eliyahu (of the Ben Ish Chai, Reish Vayigash) brilliantly explains a baffling Midrash in which Yosef rebuked Yehudah based on a deep understanding of the sale of Yosef, the episode with Tamar... Why would Hashem reveal this to Yosef through Ru'ach ha'Kodesh? Perhaps Yosef overheard the brothers saying 'this is Midah k'Neged Midah for this....' (PF)
Rashi (to 43:33; refer to 43:33:1:1) explains that he seated them based on order of birth. Ha'amek Davar (loc. cit.; refer to 43:33:151:1) holds that he seated them also based on authority and importance.
QUESTIONS ON RASHI
Rashi writes: "'My Gavi'a' - a long (i.e. tall) cup." How is this derived?
Gur Aryeh: "Gavi'a" comes from the same root as 'Giv'ah' - 'hill,' implying a cup that is tall like a mountain.
