Umpteen massacres and a wedding. So romantic.
Judah and Simeon decide to try and rid Canaan of its pesky inhabitants. They kill 10 000 Perizzites and Canaanites at Bezek. Someone named Adonibezek flees and has his thumbs and big toes cut off as a result. This apparently is a revenge strategy, because he once cut the thumbs and toes off 70 kings and made them eat scraps from under his table. He is sent to Jerusalem, where he dies.
Next, the fighting force goes to Jerusalem, where they kill everybody and burn the city. Judah then goes and fights the peoples of the valleys around Hebron and turns to the city of Debir. Yes, we already heard this story. Caleb offers his daughter Achsah to anyone who can defeat the city of Karjathsepher and Othniel succeeds. She asks her father for a field and spring of water and he gives it to her. It seems like at least one of those passages could have been cut without losing any narrative clarity. In fact, it would have made the whole thing clearer.
In a weird interlude, Moses' heretofore unknown Kenite father in law head out into the wilderness. Judah's people then go kill more Canaanites. They take over three more cities, but are unable to conquer a tribe that has iron chariots. So in this little game of rock-paper-scissors we've got going here, iron chariots beat god, god beats unicorns. I'm hoping unicorns will eventually turn out to beat iron chariots. And also wondering why we don't worship chariots, since they're clearly the superior beings here.
Then, even though we've been told just a few verses ago that Jerusalem has been defeated and burnt to the ground, we find out the Benjaminites can't take it.
Joseph's people go to Bethel and a man comes to meet them. He agrees to show them the entrance to the city in exchange for his life.
There are a bunch of other failed conquests in all the other areas as well but it doesn't seem interesting enough to list them here.