This volume collects contributions on the theme of prolepsis in Antiquity, Middle Ages, and Renaissance. As the interest in this topic grows, our goal is to provide a first attempt at adopting an all-encompassing approach, which thematizes prolepsis as a pivotal hermeneutic tool to “read” into different times and contexts. While the first section maintains a more traditional literary approach to the topic, the second section hosts a reflection on the relationship between prolepsis and kingship within historiographical accounts. The chapters of the third section revolve around a religious interpretation of prolepsis, creating an overview of theological practices and narrations connected to foreshadowing through time. Section four hosts chapters that differ significantly in their individual fields but share the common understanding of a practical application of prolepsis in the ancient Greek world, with a specific technical focus. The three essays of the fifth and final section explore entirely different conceptualizations, delving into alternative notions of prolepsis, combining approaches and maintaining a more methodological focus.