This chapter examines the compunctious hymns of Romanos the Melodist. It explores the genre of his compositions (kontakion) and their liturgical context, reimagining the performance of his hymns during the Lenten period. It does so according to three themes: compunction and repentance; biblical exemplars of compunction; and compunction in the face of eschatological judgment. By framing the approach of this chapter with these three themes, the most relevant elements of compunction in Romanos’ oeuvre are examined. The chapter shows how Romanos’ kontakia, by retelling and amplifying the sacred stories that defined the Byzantines, sought to frame and shape an emotional and liturgical community in Constantinople.