Hebrews scholars have noted the significance of the Christological titles, ἀρχηγός and πρόδρομος, in the author’s argument (2:10; 6:19; 12:2). However, an Old Testament background has remained elusive, leading many to favor a Hellenistic origin for the terms. This study argues that the story of the Kadesh rebellion (Numbers 13–14) is the background for both terms. Considering the story’s prominence in the argument of Hebrews 3–4, this coheres with the author’s rhetorical use of wilderness imagery. As a minority of Hebrews scholars have pointed out, the spies of Numbers 13 bear the title ἀρχηγοὶ (Num 13:2, 3). Independently, commentators on Deuteronomy’s retelling of the Kadesh events (Deut 1:19-46) have noted that Deut 1:22 and 1:33 juxtapose the spies with Yahweh himself. The people demand men to “go before us” (προτέρους ἡμῶν) to show “by which way we must go up.” In the end, Moses castigates the people for failing to trust in Yahweh who was himself “going before you” (προπορεύεται πρότερος ὑμῶν), to spy out the land (Heb: תור; cf. Num 13:2, 16, 17, 21, 25, 32; 14:6, 7, 34, 38) and show “by which way you must go up.” In the Deuteronomic narrative, Yahweh is the divine forerunner who goes before Israel to grant access to the land by driving out its inhabitants, thus eliminating the barriers to Israel’s entry and inheritance. I argue that this coheres with the function of the titles in Hebrews, where Christ is the access-granting divine scout (ἀρχηγός) and forerunner (πρόδρομος), who enables entry into the land by removing the barriers to his people’s access (Heb 4:10; 6:19–20; 9:8; 10:19–22).