Genesis 44 continues the dramatic account of Joseph testing his brothers who have come to Egypt seeking grain during the famine. At the beginning of the chapter, Joseph instructs his steward to fill his brothers' sacks with grain and to secretly place each man's money back in his sack. Most significantly, he orders that his personal silver cup be hidden in Benjamin's sack, the youngest brother who is Jacob's beloved son and Joseph's only full brother.

After the brothers leave the city, Joseph sends his steward to pursue them with an accusation of theft. The steward confronts them about stealing his master's silver cup, which he claims is used for divination. The brothers vehemently deny the accusation and confidently declare that whoever is found with the cup should die, while the rest should become slaves. However, the steward proposes a more lenient punishment: only the guilty party would become a slave while the others could go free.

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

Back in Joseph's presence, Judah takes the lead as spokesman for his brothers. He acknowledges their apparent guilt while maintaining their innocence, recognizing that God has somehow exposed their past sins. When Joseph insists that only Benjamin needs to remain as his slave, Judah explains that their father Jacob's life is bound up with Benjamin's welfare, describing how Jacob had lost one beloved son (Joseph) and how losing Benjamin would kill him. Judah says that he cannot bear to see his father's grief and asks to substitute himself for Benjamin so that the young man can return home.