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Genesis 44 continues the account of Joseph testing his brothers who came to Egypt seeking grain during the famine.

Joseph instructed his steward to fill his brothers' sacks with grain and to secretly place each man's money back in his sack. Most significantly, he ordered that his personal silver cup be hidden in Benjamin's sack, the youngest brother who was Jacob's beloved son and Joseph's only full brother.

After the brothers left the city, Joseph sent his steward to pursue them with an accusation of theft. The steward confronted them about stealing his master's silver cup, which he claimed was used for divination. The brothers vehemently denied the accusation and confidently declared that whoever was found with the cup should die while the rest should become slaves. However, the steward proposed a more lenient punishment: only the guilty party would become a slave while the others could go free.

When the sacks were searched from oldest to youngest, the cup was discovered in Benjamin's possession. The brothers were devastated and tore their clothes in anguish. They all returned to the city together, refusing to abandon Benjamin despite being given the opportunity to leave without him.

Back in Joseph's presence, Judah took the lead as spokesman for his brothers. He acknowledged their apparent guilt while maintaining their innocence, recognizing that God had somehow exposed their past sins. When Joseph insisted that only Benjamin needed to remain as his slave, Judah explained that their father Jacob's life was bound up with Benjamin's welfare, describing how Jacob had lost one beloved son (Joseph) and how losing Benjamin would kill him. Judah said that he couldn't bear to see his father's grief and asked to substitute himself for Benjamin so that the young man could return home.