Adam Clarke on Joshua 14:13

Joshua blessed him - As the word bless often signifies to speak good or well of or to any person, (see the note on Gen 2:3), here it may mean the praise bestowed on Caleb's intrepidity and faithfulness by Joshua, as well as a prayer to God that he might have prosperity in all things; and especially that the Lord might be with him, as himself had expressed in the preceding verse.