Many have assumed that the anonymous Letter to the Hebrews is the most supersessionistic text in the entire New Testament. Recent studies by Gelardini, Eisenbaum, and Anderson have shown that the socio-cultural context of Hebrews was far more complex than scholars previously grasped, resulting in a very different picture regarding Hebrews’ portrayal of Israel: Jewish-Christian relations were disturbed and disjointed, and the search for religious identity was ongoing (not settled). Such studies have shown the nuance in the anonymous writer’s approach to thinking about the Jewish religion in light of Jesus of Nazareth. This tendency to rethink Hebrews in light of its socio-cultural context might be supplemented by turning focus to another topic (too often overlooked in discussions of supersessionism in Hebrews): the Sabbath. What if the standard supersessionistic reading of Sabbath in Hebrews was wrong (in light of the canonical sequence implied by the quote from Ps. 95 in Heb. 4:3 as well as the formal structure of this section of the letter)? Might this shape our understanding of Jewish-Christian self-understanding in the latter first century? This paper explores these possibilities by offering an exegesis of Hebrews 3:7-4:13 and then attempting to assess the validity of reading Hebrews as supersessionistic. It considers this section within the argument of the whole letter (looking especially to the programmatic comments in the exordium as well as the imitative exhortations found in chs. 11-12). It will be suggested that grasping the relationship of Hebrews to supersessionism involves coming to terms with the nature of typology in this Epistle.