The peculiar iconography of the winged horse surmounted by several puttos, as appears in the Hypnerotomachia Poliphili sixth woodcut, turns out to be unprecedented and enigmatic at a glance and it’s the result of the depth and complexity of the author’s concepts. Considering the iconographic details of the sculptural group as well as the text scattered with allusions to the classical and humanistic sources, the symbology of the winged horse is brought back to the pertinent context of ambiguity between Fortune and misfortune, which acts as interpretation setting for the symbolic imaginary at the beginning of Poliphilo’s journey of initiation. In particular, the symbology of the horse, interpreted as horse of the lost Fortune, is confirmed th...