Scholarly study of the Letter to the Hebrews over the last century has devoted a great deal of attention to the use of the Old Testament within the Christian text. Such attention has focused upon diverse issues such as the source Vorlage available to the author, his exegetical and hermeneutical methodologies, and his treatment of themes such as priesthood, covenant, cult, rest or eschatology. Occasionally, scholars have produced substantive analysis of the use of particular texts, such as Ps 110, or Jer 31, but comparatively little attempt has yet been made to assess how an entire narrative or book functions within the letter. Bearing this in mind, this thesis examines the way in which the book of Deuteronomy operates within the paraenetic sections of Hebrews, both at a micro-level (in terms of citation or allusion to the prior text) and at a macro-level (how broad Deuteronomic themes are treated within the discourse). There is extensive treatment of Deuteronomic quotations and echoes, as well as analysis of Hebrews’ borrowing of Deuteronomy’s covenantal blessing/cursing imagery. The thesis also focuses on the way in which Hebrews shares Deuteronomy’s sermonic tone and paraenetic urgency, and how both texts rhetorically position their audience at the threshold of entry into their salvation goal, typified by the promised land. It discusses how Hebrews replays Deuteronomy’s use of the wilderness generation as the paradigm of covenantal disobedience and how both texts exhibit a complex interweaving of the past, present and future moments. Finally, it examines the extent to which Hebrews stands in the tradition of ‘re-presentations’ of Deuteronomy, echoing the way in which other 2nd Temple Jewish texts alluded to it for the purposes of their respective communities.