And put my cup, the silver cup, in the sack’s mouth of the youngest, and his corn money. And he did according to the word that Joseph had spoken. Genesis 44:2

Chapter 44 continues with the interaction between Joseph and his brothers, they all have just shared in a big feast and now they are ready to be heading home. At this point, they still don’t realize that the ruler of Egypt is their own brother Joseph. So before he sends them away Joseph is going to test them another time. He puts a valuable silver cup in the youngest brothers (Benjamin) belongings

And he said, Now also let it be according unto your words: he with whom it is found shall be my servant; and ye shall be blameless. Genesis 44:10

Joseph confronts them about stealing the silver cup, but at this point the brothers have no idea what he is talking about. Joseph told them whoever has the cup will be his slave, this is obviously another test for their youngest brother Benjamin

And we said unto my lord, The lad cannot leave his father: for if he should leave his father, his father would die. Genesis 44:22

Judah tries to plead with Joseph , that if he takes Benjamin as a slave his father will die. Remember Judah promised his father that he would bring Benjamin back safely. Little does Judah realize that Joseph is testing his brothers

And the one went out from me, and I said, Surely he is torn in pieces; and I saw him not since: Genesis 44:28

Jacob is still mourning the loss of Joseph, he still doesn’t realize that Joseph never died. This I believe is what Joseph was trying to find out, if his father and family missed him after all this time. Judah is pleading with Joseph to release Benjamin so it doesn’t destroy his father, well see in the next Chapter what happens!