A moment of profound crisis unfolds when Reuben returns to the location where his brother was abandoned, only to discover a drastically altered reality. Finding the pit empty strikes him with shock, prompting a bitter cry over the heavy responsibility resting on his shoulders. Commentators explore several reasons why Reuben was missing during the sale to the Ishmaelites. One approach suggests he deliberately distanced himself so his brothers would not suspect his true intentions. He waited for them to move away or become occupied with their meal, planning to take a detour and secretly pull his brother to safety to return him to their father. However, the lengthy route or the unpredictable arrival of merchant caravans caused him to miss his opportunity [מלבי״ם, ביאור יש״ר, העמק דבר, צרור המור]. Conversely, another perspective argues that Reuben never intended to smuggle him out, knowing the brothers would immediately notice and give chase. Instead, he had only left to fetch food and water to bring to the pit with their permission [קונטרס חיבה יתירה].
Other interpretations tie his absence to personal and familial obligations. Some suggest it was Reuben's scheduled turn to go home and attend to their father, Jacob [רש״י]. Since Jacob still had to send Joseph to check on the brothers, this rotation likely occurred only once every few days [משכיל לדוד, ברכת אשר]. A prominent explanation is that Reuben was occupied with fasting and wearing sackcloth as part of a private repentance process for previously disturbing his father's bed [רש״י, פני דוד]. His public confession for this act would only come much later, following Judah's confession [מזרחי, שפתי חכמים, הדר זקנים, דעת זקנים]. This earlier transgression was not inherently malicious but stemmed from acting too hastily to defend his mother's honor, and he rushed to repent for that impulsiveness [בית הלוי]. He may have chosen to isolate himself in fasting at that specific moment, hoping that the merit of saving his brother would help secure his father's forgiveness [ברכת אשר]. Furthermore, witnessing a young boy suffer such a severe fate made Reuben realize that divine punishment could strike before the age of twenty, sparking an anxiety that accelerated his own repentance [פרדס יוסף].
Upon arriving at the empty pit, Reuben immediately assumes his brother has been killed or devoured by a wild animal [העמק דבר, צרור המור]. Overcome with deep sorrow and concern for the boy's fate, he tears his garments [ביאור שטיינזלץ]. However, unlike his father Jacob, who would later tear his clothing all the way down to his skin, Reuben only tore his outer layers [הטור הארוך].
Reuben's distress is uniquely profound compared to the rest of the brothers. As the firstborn, he knew Jacob would hold him personally responsible and demand he search the entire world for the missing boy. Had his brother simply died in the pit, Reuben could have at least presented the body as proof of a wild animal attack; with him completely vanished, he was left without any answer [אור החיים]. A heavy burden of guilt also weighed on him, as he was the one who initially suggested throwing the boy into the pit, making him feel directly responsible for the tragic outcome [צרור המור]. Additionally, he feared Jacob would suspect him of orchestrating a murder to reclaim his lost birthright [הדר זקנים]. On a spiritual level, Reuben felt his previous sin had already fractured the completeness of the twelve tribes, and this new loss amplified the void, bearing down heavily on his conscience [פני דוד].
Reuben's swift return and bitter cries left the other brothers with little time to deliberate. To conceal the disappearance before Reuben could take any further action, they were forced to immediately slaughter a goat and dip the boy's tunic in its blood. This hasty cover-up ultimately served as a measure-for-measure punishment for Jacob, who had once deceived his own father, Isaac, using the skins of goats [צרור המור].