1 And he commanded the steward of his house, saying, “Fill the men’s sacks with food, as much as they can carry, and put each man’s money in the mouth of his sack.
2 Also put my cup, the silver cup, in the mouth of the sack of the youngest, and his grain money.” So he did according to the word that Joseph had spoken.
3 As soon as the morning dawned, the men were sent away, they and their donkeys.
4 When they had gone out of the city, and were not yet far off, Joseph said to his steward, “Get up, follow the men; and when you overtake them, say to them, ‘Why have you repaid evil for good?
5 Is not this the one from which my lord drinks, and with which he indeed practices divination? You have done evil in so doing.’ ”
6 So he overtook them, and he spoke to them these same words.
7 And they said to him, “Why does my lord say these words? Far be it from us that your servants should do such a thing.
8 Look, we brought back to you from the land of Canaan the money which we found in the mouth of our sacks. How then could we steal silver or gold from your lord’s house?
9 With whomever of your servants it is found, let him die, and we also will be my lord’s slaves.”
10 And he said, “Now also let it be according to your words; he with whom it is found shall be my slave, and you shall be blameless.”
11 Then each man speedily let down his sack to the ground, and each opened his sack.
12 So he searched. He began with the oldest and left off with the youngest; and the cup was found in Benjamin’s sack.
13 Then they tore their clothes, and each man loaded his donkey and returned to the city.
14 So Judah and his brothers came to Joseph’s house, and he was still there; and they fell before him on the ground.
15 And Joseph said to them, “What deed is this you have done? Did you not know that such a man as I can certainly practice divination?”
16 Then Judah said, “What shall we say to my lord? What shall we speak? Or how shall we clear ourselves? God has found out the iniquity of your servants; here we are, my lord’s slaves, both we and he also with whom the cup was found.”
17 But he said, “Far be it from me that I should do so; the man in whose hand the cup was found, he shall be my slave. And as for you, go up in peace to your father.”
18 Then Judah came near to him and said: “O my lord, please let your servant speak a word in my lord’s hearing, and do not let your anger burn against your servant; for you are even like Pharaoh.
19 My lord asked his servants, saying, ‘Have you a father or a brother?’
20 And we said to my lord, ‘We have a father, an old man, and a child of his old age, who is young; his brother is dead, and he alone is left of his mother’s children, and his father loves him.’
21 Then you said to your servants, ‘Bring him down to me, that I may set my eyes on him.’
22 And we said to my lord, ‘The lad cannot leave his father, for if he should leave his father, his father would die.’
23 But you said to your servants, ‘Unless your youngest brother comes down with you, you shall see my face no more.’
24 “So it was, when we went up to your servant my father, that we told him the words of my lord.
25 And our father said, ‘Go back and buy us a little food.’
26 But we said, ‘We cannot go down; if our youngest brother is with us, then we will go down; for we may not see the man’s face unless our youngest brother is with us.’
27 Then your servant my father said to us, ‘You know that my wife bore me two sons;
28 and the one went out from me, and I said, “Surely he is torn to pieces”; and I have not seen him since.
29 But if you take this one also from me, and calamity befalls him, you shall bring down my gray hair with sorrow to the grave.’
30 “Now therefore, when I come to your servant my father, and the lad is not with us, since his life is bound up in the lad’s life,
31 it will happen, when he sees that the lad is not with us, that he will die. So your servants will bring down the gray hair of your servant our father with sorrow to the grave.
32 For your servant became surety for the lad to my father, saying, ‘If I do not bring him back to you, then I shall bear the blame before my father forever.’
33 Now therefore, please let your servant remain instead of the lad as a slave to my lord, and let the lad go up with his brothers.
34 For how shall I go up to my father if the lad is not with me, lest perhaps I see the evil that would come upon my father?”
Morris takes a stab at why Joseph orchestrated the events of this chapter. I believe it makes sense if God was the one making the test.
[Joseph’s brothers] had already shown real sorrow for their sin against Joseph, had confessed it as sin, and had also shown themselves to be honest, God-fearing men. … Furthermore, they had shown no resentment against Benjamin, as Joseph feared might be the case.
But he still was not sure what their attitude might be if forced to make a choice between their own personal welfare and that of Benjamin and their father. Accordingly, Joseph planned one further test before he could completely accept and forgive them (and, though Joseph was the man responsible, it can better be regarded as a final examination that God Himself was placing on them). — Morris, page 611.
The use of the pronoun [“this” in v. 5] without reference to any antecedent, would indicate that [the steward] believed they all knew full well what it was they had stolen. Joseph had a well-deserved reputation for prophetic insight, and the brothers themselves had noted with wonder how Joseph had been able to have them seated at the table in order of their respective ages. The inference seems to be that this may well have been an object coveted by many. …
It is known that the Egyptians used such cups, as did other ancient peoples, for the purpose of predicting, professing to see tokens of future events in the reflections of water in the cup or in the arrangements assumed by small particles of gold or silver in it. … It is probably that Joseph … was simply adapting his image to that expected of an Egyptian leader who had priestly functions as well as political. — Morris, pages 612-613.
The final evidence that their characters had indeed really be transformed by this time, was that, to a man, they were willing to stand by Benjamin no matter what! They all “rent their clothes” in grief , but immediately turned around and went back to Joseph’s city. …
Joseph opened the interview with a formal charge and inquiry as to why they had done such a thing. …
Judah was clearly the spokesman for the brothers from this time on. … He confessed their recognition that they all deserved punishment. Even though they were innocent in this particular situation, they were very guilty sinners, and “God hath found out the iniquity” of them all. He and his brothers were deeply burdened with the enormity of their deed in selling Joseph into bondage twenty years ago; now, it was only fitting that they themselves should also become slaves in Egypt for the rest of their days. — Morris, pages 615-616
Judah spoke very respectfully, but very earnestly and intensely. … He demonstrated that, whatever may have been his earlier weaknesses, whether resentment of Joseph (though it will be recalled that he at the time had saved Joseph’s life) or the lusts of the flesh (which had showed up especially in his dealings with Tamar), he now was a strong man of godly character and compassion. — Morris, page 617.
Judah had promised Israel he would be surety for Benjamin, perhaps not fully realizing at the time how near this promise would come to fulfillment. … Judah’s intense love for his father is exhibited most of all in his final plea: “How shall I go up to my father, and the lad be not with me? How can I see the evil that shall come on my father?” — Morris, page 618.
The brothers return to Joseph’s house, where Judah—whose preeminent role is anticipated by the statement “Judah and his brothers” in v.14—steps forward to intercede for the life of his brothers (v.18). After summarizing the entire situation (from 42:13), Judah draws his plea to a conclusion in v.32 by telling Joseph that he has become surety for Benjamin—again employing the verbal form of the same root used nominally in 38:17-18 to denote Judah’s “surety” or “pledge.” Whereas in this latter passage, however, the “surety” consists of certain inanimate possessions (i.e., Judah’s seal, cord, and staff), in the present passage it consists of the person of Judah himself—the theological-Christological significance of which is vividly borne out by use of the nominal form of this same root applied in the New Testament to the “surety” of believers as centered in Jesus and represented by His abiding Spirit (so in all 3 NT occurrences: 2 Corinthians 1:22; 5:5; Ephesians 1:14). Indeed, this messianic significance of the term—and hence of Judah typologically—is already expressed in the Hebrew Bible in the Lord’s eschatological declaration through Jeremiah (in Jeremiah 30:21) that He will one day reconcile His people Israel to Himself because “their leader (who) shall be one of them … will give Himself in surety” for them. — Wechsler, page 259.