Genesis 44:2

“And put my cup, the silver cup, in the sack’s mouth of the youngest, etc.] Benjamin; this he ordered to be done, partly to put him in apparent danger, and try how his brethren would behave towards him in such circumstances, and thereby know how they stood affected to him; and partly that he might have an excuse for retaining him with him. This cup was valuable both for the matter of it, being of silver, and for the use of it, being what Joseph himself drank out of: and by the word used to express it, it seems to have been a large embossed cup, a kind of goblet, for it has the signification of a little hill. Jarchi says it was a long cup, which they called “mederno”. The Septuagint render it…”

“put my cup, the silver cup, in the sack's mouth--It was a large goblet, as the original denotes, highly valued by its owner, on account of its costly material or its elegant finish and which had probably graced his table at the sumptuous entertainment of the previous day.”

“- The Ten Brothers Were Tested Joseph has had the satisfaction of seeing his brother Benjamin safe and well. He has heard his brothers acknowledging their guilt concerning himself. He resolves to put their attachment to Benjamin, and the genuineness of their change of disposition, to a test that will at the same time expose Benjamin to no hazard. Genesis 44:1-5 And my cup. - Besides returning each man’s money as before, a silver cup of Joseph’s is put in Benjamin’s bag, after which, when daylight comes, they are dismissed. They are scarcely out of the town when Joseph’s steward is ordered to overtake them, and charge them with stealing the cup. “And whereby indeed he divineth.” Divining by…”

“44:2 Joseph was giving his brothers the chance to abandon Benjamin if they wanted to. Joseph was testing them to see if they were loyal to the family and faithful to their father.”