Contradiction with Genesis 12:6
God promised the land to Abram's descendants, implying initial occupation, whereas Joshua 15:44 suggests it was assigned to Judah later.
Genesis 12:6: And Abram passed through the land unto the place of Sichem, unto the plain of Moreh. And the Canaanite [was] then in the land. [plain: Heb. plains]
Contradiction with Numbers 32:33
This verse shows the land allocated to the tribes of Gad and Reuben, not Judah, which is a different tribe from Joshua 15:44.
Numbers 32:33: And Moses gave unto them, [even] to the children of Gad, and to the children of Reuben, and unto half the tribe of Manasseh the son of Joseph, the kingdom of Sihon king of the Amorites, and the kingdom of Og king of Bashan, the land, with the cities thereof in the coasts, [even] the cities of the country round about.
Contradiction with Judges 1:21
The Jebusites lived in Jerusalem among the people of Judah, contradicting the claim of exclusive occupation secured by Joshua.
Judges 1:21: And the children of Benjamin did not drive out the Jebusites that inhabited Jerusalem; but the Jebusites dwell with the children of Benjamin in Jerusalem unto this day.
Contradiction with 1 Kings 12:17
The real control of the land, including Judah, is questioned during the divided monarchy, unlike the unified allocation in Joshua 15:44.
1 Kings 12:17: But [as for] the children of Israel which dwelt in the cities of Judah, Rehoboam reigned over them.
Contradiction with Ezekiel 48:1
This allocation of land in a vision does not include Keilah in Judah, contradicting Joshua 15:44's earthly allocation.
Ezekiel 48:1: Now these [are] the names of the tribes. From the north end to the coast of the way of Hethlon, as one goeth to Hamath, Hazarenan, the border of Damascus northward, to the coast of Hamath; for these are his sides east [and] west; a [portion for] Dan. [a portion: Heb. one portion]