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Caleb’s portion within the tribal territory of Judah is a special case. Caleb reminded Joshua that only the two of them had been faithful to God at the first opportunity to enter the land (Nu 14:6-9). God had promised Caleb that he would enter it. Now Caleb requested Hebron as his inheritance, with the opportunity to drive out the Anakim who had so frightened the other spies long ago. Joshua gave him Hebron as a reward for his faithfulness.
That the Anakim still could be present to challenge Caleb at Hebron after the notice of 11:21-22 is puzzling. Though Joshua had conquered Hebron in the southern campaign, Caleb had to take it again. Perhaps some of the surviving Anakim (11:22) had come back to Hebron. Or perhaps the notice of Joshua’s complete victory over them is intended to include Caleb’s victory recorded in 15:14. In any case, Caleb’s victory marked a promising beginning to the process of allotment on this side of the Jordan.