The last fifteen years has seen a renewed interest in scholarship in the faithfulness of Jesus in the Letter to the Hebrews. Many of the monographs written on this subject include analyses of Hebrews 2 and Hebrews 5, along with other key pericopes. These two chapters also contain references by the writer of Hebrews to the perfection of Jesus, another theme that receives a great deal of attention in Hebrews scholarship. However, a review of scholarship on the themes of the faithfulness and perfection of Jesus shows that, despite scholars drawing on the same passages in discussing these themes, there has been very little reflection on the possible links between these two themes. Where the faithfulness and perfection of Jesus are viewed to be related, the focus is often on Hebrews 12:2 with its description of Jesus as the perfecter of faith (τῆς πίστεως ἀρχηγὸν). Faith (πίστις) can be defined as the belief or trust which motivates a faithful (πιστός) life towards God. Many scholars come close to linking the themes of perfection and faithfulness, but this has not been followed through with deliberate reflection on the lens that the faithfulness of Jesus in Hebrews offers for understanding the writer’s comments on the perfection of Jesus. This paper provides an exegesis of Hebrews 2:6–18 and 5:7–10, and reviews recent scholarship on the faithfulness of Jesus and the perfection of Jesus in Hebrews. It proposes that these themes should be considered together, and that part of the perfection of Jesus on view in these pericopes is the demonstration of his complete faithfulness. The paper finishes by outlining how the perfectly faithful Jesus in Hebrews is the agent and exemplar of faithfulness for us, both enabling us to be faithful and demonstrating what faithfulness looks like. The perfection of Jesus’s faith is therefore an encouragement and challenge for the church today to prioritize and prize faithfulness.