To verify his new role and establish the reality of his kingship, Samuel provides Saul with a series of signs, proving that this appointment comes directly from God [מצודת דוד, אברבנאל]. The first of these signs involves a forthcoming encounter with two men who will bring him news from his home.
The location of this meeting presents a geographical puzzle. The men are described as being near Rachel's tomb, which is located in Bethlehem within the territory of Judah, yet the encounter is set to take place at the border of Benjamin. The primary approach among commentators is that the situation is dynamic. At the exact moment Samuel is speaking, the men are indeed near Rachel's tomb, but they are already traveling toward Saul. By the time the actual meeting occurs, they will have reached the border of Benjamin. Furthermore, the specific location of the encounter is understood as a hint to Jerusalem, representing the pure and clear shadow of God [רש״י].
When Saul meets these men, they will inform him that his father has completely abandoned his concern for the lost donkeys. Even before the animals were recovered, his father let go of this minor issue, becoming overwhelmed with a much greater fear for the safety of his son and his servant, who had been missing for several days [רש״י, רד״ק, מצודת דוד, ביאור שטיינזלץ]. While he certainly cared for both of them, his deepest and primary agony was reserved for his son alone, crying out in distress over what he should do for his child [אברבנאל]. This unfolding situation precisely mirrors the very fear Saul himself had expressed to his servant earlier in their journey [אברבנאל, ביאור שטיינזלץ].
Beyond the physical events, this sign contains profound hints regarding Saul's future as king. The geography of the encounter points to the ancestral merits that earned Saul the throne. These include the merit of Rachel, the merit of the tribe of Benjamin who bravely jumped into the Red Sea first, and the merit of Saul's grandfather who used to light candles in dark alleyways, a good deed subtly connected to the name of the meeting place [חומת אנך].
Conversely, the details of this meeting also serve as a moral warning. The mention of Rachel's tomb is meant to remind Saul of her death, which came as a punishment, cautioning him to avoid sin. Furthermore, just as his father abandoned his concern for livestock in favor of his son, Saul is being warned that he must one day abandon his desire for the sheep and cattle of Amalek. Instead, he must worry about God's anger if he disobeys His command [אלשיך]. Another perspective views this sign as a reflection of the nation Saul is destined to lead. The two men represent the general public, divided between those who chase physical desires and those who pursue wealth. The reference to Rachel's tomb symbolizes that their divine soul is buried deep beneath their material urges. These individuals will stand on the sidelines, preoccupied with mundane matters like the donkeys, and will fail to offer Saul true support or bring him a tribute at the beginning of his reign [מלבי״ם].