David turns to God in prayer to uncover Saul's true intentions toward the city of Keilah after receiving deeply troubling news [ביאור שטיינזלץ]. The reports reaching him come in two distinct parts. First, he learns that Saul is actively planning to march on Keilah. Second, he hears that Saul intends to utterly destroy the city [אלשיך].
The threat of destruction is not a punishment for the city having hosted David in the past. Instead, it is a calculated tactic. Saul plans to use the threat of total ruin as leverage to force the townspeople into handing David over [מלבי״ם, מצודת דוד]. This specific distinction is the root of David's dilemma. If Saul's ultimate plan is to ruin the city regardless of the circumstances, David knows he must flee immediately to save the residents, without waiting to see if they would betray him. On the other hand, if Saul's only goal is to capture him, and Saul would simply turn back if the townspeople refused to cooperate, David's decision hinges on just one factor: whether the people of Keilah will actually betray him [אלשיך, מלבי״ם].
Caught in this desperate situation, David asks God two consecutive questions: Will Saul come down, and will the people of the city hand him over? In response, God initially addresses only the first question. This follows a recognized principle that one should not present two questions at the exact same time. Believing that God withheld the second answer because the initial inquiry lacked sufficient detail, David asks again, explicitly inquiring whether he and his men will be surrendered to Saul [אלשיך, מלבי״ם].