Chisholm asks, Since when have chariots been able to thwart God’s purposes and power? The Lord destroyed the Egyptian chariots in the Red Sea (Exodus 14:23–28; Exodus 15:4). He promised to give the Canaanite chariots into Israel’s hands and instructed Joshua to burn them (Joshua 11:4–6), orders which Joshua carefully obeyed (Joshua 11:9). Later Joshua assured the men of Joseph that the Canaanite iron chariots would not prevent them from conquering the plains (Joshua 17:16–18). But here we read that the Judahites were unable to overcome the iron chariots, even though the Lord was with them!... Judges 1:19 reflects the limited and erroneous perspective of the people, not the narrator’s own interpretation.
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19 And the LORD was with Judah, and he took possession of the hill country, but he could not drive out the inhabitants of the plain because they had chariots of iron.