What does Genesis 44:1 mean?

The passage leading up to this moment brought a sense of great relief for 11 of Jacob's sons (Genesis 43:1–2). They worried the Egyptian ruler (Genesis 42:19–20) planned to falsely enslave them for stealing during their previous trip (Genesis 42:26–28). Instead, he honored them as guests in his home, giving special attention and blessing to their youngest brother, Benjamin (Genesis 43:34). Their encounter with the man ended with eating, drinking, and laughter. All was apparently well.

The men still don't know this Egyptian ruler is their long-lost brother Joseph (Genesis 37:24–28; 42:8). He has not revealed himself, and his actions are not easy to interpret. He still may be undecided about how to deal with the men who sold him into slavery many years ago. The various rebukes and challenges he has used seem like tests; that would make what happens next a final exam for his estranged family.

Appearing to send the brothers off in good standing, Joseph orders his steward to fill their sacks with as much grain as they will hold. However, he once again tells the steward to put the money each man brought to pay for the grain back into their sacks, as well (Genesis 42:25). This time, the return of the money seems to be no secret. And yet, what appears a gesture of extended kindness will reveal itself as exactly the kind of trap the brothers had feared (Genesis 43:18).