The stories read in the Bible are commonly explored and elaborated in greater depth in the liturgical hymns, homilies, and patristic writings of the Orthodox Church. 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. 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. 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.