Hebrews 6.1–6 has proved to be a nettlesome passage throughout its interpretive history. The author of Hebrews has embedded three stubborn obstacles in the path of 6.4–6, which, taken together, have made it difficult to walk an exegetically straight course. First, the text seems to describe actual members of the Christian community, not pretenders (6.4–5). Second, it seems to speak of a true falling away (6.6). And third, it warns of the real impossibility of repentance after the apostasy (6.4, 6). These three obstacles have created a series of stumbling blocks for interpreters throughout history. Perhaps as early as the Shepherd of Hermas, the belief that Christians could not repent of certain sins—based partly on Heb 6.4–6—has vexed pilgrims traveling the Way. Understandably, modern scholarship has repeatedly attempted to steer a course around these difficulties by illuminating the path with a variety of historical backgrounds, none of which has achieved anything like a consensus. This paper argues that the first-century catechetical Two Ways didactic pattern, as exemplified in the Didache, proves to be an illuminating historical background to Hebrews 6.1–6. Though not evincing literary dependence, compelling conceptual parallels exist between the Didache and Hebrews 6.1–2. Further, the descriptors in Hebrews 6.4 correspond closely with the experience of catechumens at conversion in the Didache. In this light, parapiptõ in Heb 6.6 does not refer to irreversible apostasy, but to a failure to advance on the Way of Life.