What does Judges 1:11 mean?
Judah continues its campaign to drive out all the wicked Canaanites (Deuteronomy 9:4–5) from its territory in southern Israel (Judges 1:4–10). That campaign is now focused on what is called the "hill country," south of Jerusalem. The ancient city of Hebron and its surrounding area had been promised to Caleb by Joshua.The writer of Judges will repeat the story of Caleb capturing Hebron (Judges 1:12–15) during an earlier campaign (Joshua 15:15–19). After that, Caleb turned his sights on the nearby city of Debir, formerly known as Kiriath-sepher.
Judges 1:1–20 describes the campaign of the tribes of Judah and Simeon, to drive out or destroy all the Canaanites from their large territory in southern Israel. It begins with victories over Bezek and Jerusalem. The report rehearses the former victories by Caleb and his family in the hill country. The campaign continues into the desert wilderness of the Negeb, where a group of descendants of Moses' father-in-law settles. Judah dominates the hill country but doesn't entirely evict the wicked Canaanites because of their iron chariots.
Judges 1 summarizes the early efforts of the tribes of Israel to drive the Canaanites from the land or to destroy them entirely (Deuteronomy 7:1–5; 9:4). The process starts well with a string of successes by Judah and Simeon in the south. Then the news turns sour as one tribe after another is said to have failed to drive the Canaanites out of their allotted territories. Instead, they occupy certain territories, often allowing inhabitants of the land to live among them.