Keilah was a fortified city allotted to Judah, Joshua 15:44, and it was located near the Philistine border. In the times of Nehemiah, the city was re-occupied by the Israelites returning from the captivity in Babylon, Nehemiah 3:17-18.
After hearing reports about the Philistine’s fight against Keilah, David inquires of the Lord if he should attack them, but in response, his men objected. This was possibly because they didn’t want to fight against the Philistines and fight against Saul’s army at the same time. David inquires of the Lord again and after doing so, his men are now convinced that this is God’s will.
Since Abiathar, a priest, one of Ahimelek’s sons, was now with David’s army, 1 Samuel 22:20-23, they gave them the chance to inquire of the Lord, concerning decisions that were made. The ephod was worn by the Levitical priests and inside the pockets of the ephod, there would be the Urim and Thummim. This was how they received the ‘yes’ or ‘no’ answers to their questions from the Lord, 1 Samuel 14:19.
Here again, we see just how delusional Saul has become, he thinks that God had delivered David into his hand, but the truth is that Samuel categorically told him that God had rejected him because of his sins, 1 Samuel 13:13-14 / 1 Samuel 15:23 / 1 Samuel 15:26.
After hearing that David was in Keilah, Saul calls his army together, his reason for doing so was to get his army to go against David and his men.
Unfortunately, when David inquired of the Lord concerning the possibility that the men of Keilah would deliver him to Saul, he immediately left Keilah. It’s clear that the men of Keilah feared Saul more than David, despite David delivering them out of the hands of the Philistines.
Located five miles south southeast of Hebron, was a town called Ziph which was in the hill country of Judah, Joshua 15:55. It was founded by Mesha, a son of Caleb, 1 Chronicles 2:42, and it was near this place that David twice hid from Saul, and the citizens of this place twice betrayed the secret of David’s hiding place to Saul, 1 Samuel 23:19 / 1 Samuel 26:1.
Ziph, at this time in history, was covered with a great forest, along with many caves, which was the perfect hiding place for David and his 600 men from Saul and his army.
Notice that Johnathon went to David and encouraged him in three ways, he reminds David that Saul wouldn’t be able to find him because God would protect him. He tells David that he would become king and he tells him that Saul knows this full well.
Even though he was the son of Saul, he knew that David would become king of Israel. This again shows us Johnathon’s humility in accepting God’s will for David to be Israel’s future king.
They renewed their covenant agreement with each other as before, 1 Samuel 18:3 / 1 Samuel 20:8, but sadly this would be the last time the two of them would see each other.
The Ziphites tell Saul, who is very crafty, where David is located but Saul asks them to reconfirm his location because he knows that David is very wise and cunning.
The reason for the Ziphites betrayal was because of their zeal for Saul or the fact that David levied protection money against them as he did against Nabal, 1 Samuel 25:1-44. This whole shameful episode is recorded by David in Psalm 54:1-7.
David knows the best way to not be found by your enemy is to keep moving, keep changing your location. And so, by the time the Ziphites had returned to Saul to confirm David and his men’s location, David had moved his camp to Maon. Maon is a city in the hill country of Judah, and the home of Nabal the wealthy flock master, 1 Samuel 25:4.
Notice that Saul had to call off the search for David and his men because the Philistines were attacking the land. They called the place, ‘Sela Hammahlekoth’ which possibly means ‘Rock of Smoothness’ because it was slippery, or it could mean, ‘Rock of Division’ because it was the place which came between Saul and David.
David and his men went on to live in the strongholds of En Gedi which was a safe hiding place for now. It was here that David would wait, as he said until he saw what God was going to do for him, 1 Samuel 22:3.