The brothers' departure from Egypt is abruptly cut short by a carefully orchestrated pursuit. The timing of this chase, the identity of the pursuer, and the precise nature of the accusation are meticulously designed to test the brothers, prevent their escape, and confront them with a piercing moral claim. Joseph issues an urgent directive to the steward of his house, instructing him to overtake the brothers immediately, just as they leave the city. The primary approach among commentators suggests a tactical and security-based motive for this prompt timing. The brothers were known to be immensely powerful, likened to beasts of prey. Joseph knew that once they reached the open road, no force would be able to subdue them. Therefore, it was imperative to apprehend them while the intimidating awe of the great metropolis still lingered over them [הטור הארוך, הדר זקנים, דעת זקנים].
Other perspectives offer different underlying reasons for the immediate pursuit. A spiritual motive suggests that Joseph wanted to intercept them before they traveled far enough from the city to become obligated in the Traveler's Prayer. By catching them early, he ensured they would not yet have the spiritual protection that this prayer provides against harm [פרדס יוסף]. Alternatively, the swift chase was an act of consideration, sparing the brothers the exhaustion of a long journey back [צאינה וראינה]. Another view frames the timing as a final test of their urgency. Joseph wanted to see if they would cross the permitted walking boundary for the Sabbath. If they stopped at the limit, it would indicate their situation was not desperate; however, if they continued, it would prove their family was in genuine mortal danger from starvation, justifying the continuous travel [חנוכת התורה].
The steward dispatched to chase the brothers is identified as Joseph's own son, Menashe. Because Menashe led this pursuit and caused the brothers the profound sorrow of tearing their garments in despair, his actions carried a lasting historical consequence. In the future, the territorial inheritance of the tribe of Menashe would similarly be torn and divided across both sides of the Jordan River [חזקוני]. When Menashe is sent, he is given strict instructions to catch up to them first and only then deliver his accusations face-to-face. He is deliberately told not to shout at them from a distance or brand them as thieves from afar, sparing them the humiliation of public shame before passing travelers [הכתב והקבלה].
The confrontation centers on a complex moral and logical argument: the betrayal of repaying kindness with malice. Beyond the sheer audacity of stealing from a benefactor and insulting his honor [העמק דבר], the steward deconstructs the motives behind the alleged crime. Typically, a person steals to exact revenge, yet the Egyptian ruler had only shown them extraordinary generosity. Sometimes, a person might take an item they believe is abandoned, but this was the ruler's personal, highly valued goblet. Furthermore, stealing an object specifically used for divination is fundamentally foolish, as the owner could simply use his abilities to immediately discover the culprit. By eliminating these common motives, the steward concludes that the brothers must have acted out of pure wickedness [מלבי״ם, העמק דבר].
To compound the accusation, the steward introduces his own personal frustration. The theft of such a crucial item forced him, the manager of the estate, to abruptly abandon his essential duties and personally chase after them. By drawing him away from the city, the brothers did more than just steal; they actively delayed the distribution of food to the desperate masses waiting for bread to feed their starving children. Through their reckless actions, they effectively became responsible for the suffering and potential loss of life among the hungry crowds [שפתי כהן].