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Virgil’s epic poem Aeneid is well known for its multiplicity of meanings and contradictions, often referred to as ‘ambiguity’. Many of its ambiguities pertain (sometimes implicitly) to the relationship between the legendary and mythological past that the poem narrates and the Trojan future under Augustan rule that it repeatedly foreshadows. In light of the 2025 Dutch Central Examination in Latin Language and Culture, which focuses on the relationship between Aeneas and Augustus in the Aeneid, this article provides a brief summary of the scholarly discussion on Virgilian ambiguity. I argue that the mere term ‘ambiguity’ does not suffice to accurately describe the many different aspects of ambiguity in the Aeneid, and I will introduce several additional axes and gradients to increase our grasp on the phenomenon. Finally, I discuss the figure of Aeneas’ son Ascanius as an example of how awareness of ambiguity may add to our understanding of this complex character and his role as a nexus between Aeneas and Augustus.