What does Genesis 44:4 mean?
Jacob's 11 sons have just left the city, loaded down with grain (Genesis 43:1–2; 44:1). They were surprised to be honored with a banquet (Genesis 43:34). And, apparently, they understand the Egyptian governor has given them back the money they planned to use to pay for grain (Genesis 44:1). What they don't know is that the Egyptian governor is their estranged brother, Joseph (Genesis 42:8). Nor do they know he has arranged for his personal cup to be hidden in the bag belonging to the youngest brother, Benjamin (Genesis 44:2–3).Read out of context, it would be easy to assume Joseph had a sudden change of heart about being kind to his brothers. In truth, he has planned to send his steward after his brothers all along. Joseph tells the steward to question the men harshly (Genesis 42:7) once he catches up with them. Specifically, he is to speak as if they have stolen Joseph's personal cup, accusing them once again of wrongdoing.
The brothers are innocent of any evil in this case. However, this is all part of Joseph's latest test. Twenty years earlier, these same men—except for Benjamin—had jealously sold Joseph into slavery (Genesis 37:24–28). Joseph seems to be creating another situation where the men must choose between their own desires and the good of their youngest brother.