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Judges 1:9

Adam Clarke
Bible Commentary

The Canaanites, that dwelt to the mountain - The territories of the tribe of Judah lay in the most southern part of the promised land, which was very mountainous, though towards the west it had many fine plains. In some of these the Canaanites had dwelt; and the expedition marked here was for the purpose of finally expelling them. But probably this is a recapitulation of what is related Joshua 10:36; Joshua 11:21; Joshua 15:13.

Matthew Henry
Concise Bible Commentary
The Canaanites had iron chariots; but Israel had God on their side, whose chariots are thousands of angels, Ps 68:17. Yet they suffered their fears to prevail against their faith. About Caleb we read in Jos 15:16-19. The Kenites had settled in the land. Israel let them fix where they pleased, being a quiet, contented people. They that molested none, were molested by none. Blessed are the meek, for they shall inherit the earth.
The Limits of Israelite Settlement
The Period of the Judges