בראשית, פרק מ״ב, פסוק ט״ז

Joseph subjects his brothers to a strict and fateful test, presenting a harsh condition designed to verify their identity and dismantle the suspicion that they are spies. This demand blends deep psychological pressure with a calculated tactical maneuver. At the core of this test is the requirement that one person be sent away. The primary approach among commentators is that Joseph required one brother to return to Canaan. Isolating a single brother was intended to provoke deep soul-searching among them regarding the sin of selling their own brother. Joseph anticipated that Reuben, the eldest, would be the one allowed to go free. This would lead the others to realize he was spared because he had not actively participated in their past betrayal [כלי יקר]. However, another perspective suggests the intention was not to send a brother at all, but rather to dispatch an Egyptian messenger on their behalf. According to this view, all the brothers were to remain incarcerated to prevent them from coordinating their stories with Benjamin in advance. Keeping them locked up allowed for separate interrogations to ensure their individual accounts matched [מלבי״ם].

As for those remaining in Egypt, they are ordered to be imprisoned. Since individuals cannot physically imprison themselves, this directive meant they must accept their judgment and submit to confinement, or simply that they would inevitably be thrown into prison [אבן עזרא, שד״ל, ביאור יש״ר, מחוקקי יהודה]. The ultimate goal of this imprisonment is to question their integrity and determine if they are indeed speaking the truth [רש״י, רד״ק, מזרחי, שד״ל]. Bringing their youngest brother to Egypt was meant to substantiate their highly unusual story. The brothers had previously claimed they entered the city through different gates because they were searching for a lost brother. If they could prove they truly had a younger brother who remained with their father out of fear of tragedy, it would lend credibility to their claim that they were searching for yet another missing brother [משכיל לדוד]. Furthermore, basic military logic dictates that if spies are captured, their commanders will not send another operative to rescue them. Therefore, the arrival of a young boy would confirm they were an authentic family, completely ruling out any suspicion of a military operation [ביאור שטיינזלץ].

Joseph concludes his demand with a severe threat. This warning does not merely imply a failure to send a messenger; rather, it emphasizes the failure to physically bring the boy back. The mere act of sending someone would not clear them of the espionage charges; only the actual arrival of the youngest brother could prove their innocence [רש״י, מזרחי, שפתי חכמים, דברי דוד]. Despite the uncompromising nature of the demand, the brothers did not rush to fulfill it. They knew their father Jacob would never agree to send Benjamin away with only one brother, and they feared such a request would cause him to die of grief. Furthermore, they refused to separate from one another, ensuring that no single brother would have to bear the burden of guilt alone. Instead, they chose to remain silent and endure imprisonment together, hoping the ruler's anger would eventually fade. On his end, Joseph allotted them a strict three-day window. He calculated that the mounting pressure and the agonizing worry for their starving families back home would eventually break one of them, compelling someone to retrieve Benjamin, even through deception or force [אור החיים, רש״ר הירש, ביאור יש״ר]. Ultimately, on the third day, Joseph shifted his strategy, deciding to keep only one brother in prison while sending the rest back home [צאינה וראינה].