This paper discusses ancient versions of paradoxes today classified as paradoxes of presupposition and how their ancient solutions compare with contemporary ones. Sections 1–4 air ancient evidence for the Fallacy of Complex Question and suggested solutions, introduce the Horn Paradox, consider its authorship and contemporary solutions. Section 5 reconstructs the Stoic solution, suggesting the Stoics produced a Russellian-type solution based on a hidden scope ambiguity of negation. The difference to Russell’s explanation of definite descriptions is that in the Horn Paradox the Stoics uncovered a hidden conjunction rather than existential sentence. Sections 6 and 7 investigate hidden ambiguities in “to have” and “to lose” and ambiguities of quantification based on substitution of indefinite plural expressions for indefinite or anaphoric pronouns, and Stoic awareness of these. Section 8 considers metaphorical readings and allusions that add further spice to the paradox.