The Orthodox Church understands the Holy Scriptures to be the fountainhead of Tradition. The stories read in the Bible are commonly explored and elaborated in greater depth in liturgical hymns, homilies, and patristic writings. Such is the case with the account found in St Luke’s gospel of a sinful woman who anoints Christ with precious oil shortly before his Passion and Crucifixion. The woman’s story is taken up in the liturgical tradition of the Orthodox Church in Holy Week, where she is held up as an example of repentance and unconstrained love. In this in-depth but readable study the biblical accounts are elaborated through both the liturgical and oratorical tradition of the Church, as found primarily in Greek and Syriac manuscripts, with particular attention given to the former texts, too often overshadowed by the latter. Previously inaccessible texts of late antiquity, such as homilies by Amphilochius of Iconium and Ephrem Graecus, are found here in English for the first time, together with fresh English renderings of other sermons. This sharply honed and well-constructed work will engage all who encounter the story of the sinful woman in the living tradition of worship in the Orthodox Church, as well as those who are introduced to her through Scripture, liturgical poetry, or scholarly consideration. The present work unveils the intricate nature of the tradition of the Church, which gives greater scope and application to the biblical record through its hymnography and oratory.