Moments before releasing his brothers to return home, Joseph orchestrated a highly calculated psychological, legal, and educational test. He instructed his steward to fill the brothers' personal bags to the absolute brim, providing far more grain than their money could buy [רמב״ן, רבנו בחיי, הטור הארוך, ביאור ישר, ביאור שטיינזלץ, העמק דבר]. Unlike their previous journey where their payment was returned secretly, this time the money was placed back in their sacks with their full awareness, ensuring they would not be surprised later [ברכת אשר]. On the surface, Joseph presented this refund as a gesture of goodwill and compensation for the distress they had previously endured [ספורנו, הטור הארוך].
Beneath this apparent generosity lay a brilliant legal strategy. Joseph planned to plant his personal goblet in Benjamin's bag. Had he returned their money secretly, the brothers could have later argued that just as the money appeared without their knowledge, the goblet must have been a similar mistake. Refunding their money openly and officially stripped them of this defense [רמב״ן, רבנו בחיי, צאינה וראינה]. Furthermore, Joseph designed this scheme to distress them without causing actual physical or financial harm [רד״ק]. The shame of being accused of theft was meant to atone for the sin of selling him, subtly hinting that someone was aware of their hidden past [אור החיים]. It also served as the ultimate test to see if they would sacrifice themselves for Benjamin, thereby proving their true brotherhood and verifying that the young man was indeed Benjamin and not an imposter [צאינה וראינה בשם חזקוני, אלשיך].
The open return of the money served profound spiritual purposes as well. It ensured the exact fulfillment of Joseph's prophetic childhood dream about the sheaves. Had the brothers simply purchased the grain, their bowing would have been nothing more than standard courtesy to a powerful official. By receiving the grain for free, their bowing transformed into an act of genuine submission [הכתב והקבלה]. Additionally, the unusual refund was designed to make the brothers feel that divine providence was miraculously intervening in their lives. Consequently, the moment the goblet was discovered, they would immediately recognize that God was exposing their past guilt [קונטרס חיבה יתירה].
Executing this plan required precise timing and a reluctant accomplice. Taking advantage of the brothers' grogginess from the wine served at his feast, Joseph had his servants load the donkeys while the men were still inside. Escorted out at dawn by guards, the brothers had no time or privacy to inspect their belongings [אלשיך]. For the steward tasked with carrying out these orders, the mission was deeply troubling. While he happily provided the generous portions of food, framing an innocent man went against his nature. As an honest official managing a fair and reliable government trade system, he recoiled at an act that appeared entirely unjust. Ultimately, Joseph had to issue a strict and forceful decree to ensure his steward carried out the plan in full [העמק דבר, רש״ר הירש].