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My boy asked me a tricky question I was unable to answer - please help. He just returned from a trip to Rome and went through the airport security checking the bags reading the Parashat Shavua (Miketz 42) about checking the bags.

The brothers were frightened by the fact that their own money was secretly returned to their luggage:

"וַיִּפְתַּח הָאֶחָד אֶת־שַׂקּוֹ לָתֵת מִסְפּוֹא לַחֲמֹרוֹ בַּמָּלוֹן וַיַּרְא אֶת־כַּסְפּוֹ וְהִנֵּה־הוּא בְּפִי אַמְתַּחְתּוֹ׃
וַיֹּאמֶר אֶל־אֶחָיו הוּשַׁב כַּסְפִּי וְגַם הִנֵּה בְאַמְתַּחְתִּי וַיֵּצֵא לִבָּם וַיֶּחֶרְדוּ אִישׁ אֶל־אָחִיו לֵאמֹר מַה־זֹּאת עָשָׂה אֱלֹקים לָנוּ

How come they didn't learn from that and didn't check the bags the second time they left Yossef and let Binyomin keep the cup?

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    I think I almost posted this question last year.
    – Alex
    Dec 8, 2018 at 22:38

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The Malbim 44:3 does note that Yosef was concerned that they would check their bags, so he decided to have their bags filled during the night and set them off in the early morning when they wouldn't be able to see well. They then were told to come back very quickly, so they really didn't have a chance to check with proper light.

Text of Malbim:

ג)"הבקר אור". שלנו בבית יוסף, ובלילה מלא אמתחותיהם אוכל ושם הכסף והגביע, וירא פן ימשמשו וימצאו, לכן שלחו באור הבוקר:

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    Thanks, I would still expect them to check the moment they set to move. I think they did realize the potential of a hoax.
    – Al Berko
    Dec 9, 2018 at 7:27
  • Interesting....
    – יהודה
    Dec 21, 2020 at 18:06

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