The narrative of Judah and Simeon's continued conquests is primarily found in the Book of Judges, specifically in Judges 1:1-20. This account follows the death of Joshua, the leader who succeeded Moses and led the Israelites into the Promised Land. With Joshua's passing, the tribes of Israel sought guidance from the LORD on who should lead the charge against the remaining Canaanite inhabitants. The LORD designated the tribe of Judah to go first, promising them victory over their enemies.

Judah's Leadership and Alliance with Simeon

Judah, recognized for its leadership among the tribes, invited the tribe of Simeon to join in the military campaign. This alliance was strategic, as both tribes shared territorial boundaries and common interests in securing their allotted inheritances. Judges 1:3 records this collaboration: "Then the men of Judah said to their brothers the Simeonites, 'Come up with us into the territory allotted to us, and we will fight against the Canaanites. We in turn will go with you into your territory.' So the Simeonites went with them."

Conquest of Bezek and Capture of Adoni-Bezek

The initial target of their campaign was the Canaanite city of Bezek. The LORD granted Judah and Simeon success, as they defeated ten thousand men at Bezek. During this battle, they captured Adoni-Bezek, a local king known for his cruelty. Judges 1:6-7 recounts his fate: "Adoni-Bezek fled, but they pursued him, seized him, and cut off his thumbs and big toes. Adoni-Bezek said, 'Seventy kings with their thumbs and big toes cut off used to gather scraps under my table. As I have done, so God has repaid me.' They brought him to Jerusalem, where he died."

Capture of Jerusalem and Further Victories

Following the victory at Bezek, the men of Judah attacked Jerusalem, capturing and setting the city ablaze. This conquest, however, was not permanent, as later accounts indicate the Jebusites continued to inhabit Jerusalem until the time of King David. The campaign continued with further victories in the hill country, the Negev, and the western foothills. Notably, they captured Hebron, defeating the descendants of Anak, and Debir, previously known as Kiriath-sepher.

Caleb's Role and the Capture of Debir

Caleb, a prominent figure from the tribe of Judah and one of the original spies sent by Moses, played a significant role in these conquests. He offered his daughter Achsah in marriage to whoever captured Kiriath-sepher. Othniel, Caleb's younger brother, successfully captured the city and received Achsah as his wife. Judges 1:15 highlights Achsah's request for additional land: "She replied, 'Give me a blessing. Since you have given me land in the Negev, give me springs of water as well.' So Caleb gave her both the upper and lower springs."

The LORD's Faithfulness and Israel's Challenges

The continued conquests of Judah and Simeon underscore the LORD's faithfulness in fulfilling His promises to the Israelites. Despite the victories, the narrative also foreshadows the challenges Israel would face due to incomplete obedience. The failure to fully drive out the Canaanites would later lead to significant spiritual and moral challenges for the nation. Nevertheless, the account of Judah and Simeon's conquests serves as a testament to the LORD's provision and the importance of faithfulness to His commands.