In the first of his series of poems, the Heroides, Ovid attempts to re-write Penelope’s story from her own perspective. The first-person account of her experiences seem at first to be somewhat straightforward: in using her own voice, she gains a degree of agency and creates her own narrative both dependent on and independent of the Odyssey. However, in examining the ways in which Ovid wields her character within an elegiac setting, the result is a much more ambiguous Penelope who sometimes resembles her Homeric counterpart, while other times directly challenges it. Exactly how Ovid creates this ambiguity is the main focus of this paper.