Resumen: Recent bibliography on Machiavelli has stressed his republicanism. Hence a lot of work has been devoted to Machiavellian concepts that can be linked to this reading: conflict, democracy, radicalism, participation. For this reason, some Machiavellian classic concepts have been neglected. In this article, I will present a new interpretation of the concept of occasione. The purpose of my article is twofold. In the first place, I will try to expand the regular reflection on this concept. Besides The Prince’s classical references, I will pay attention to the thoughts Machiavelli devotes to this concept in L’arte della guerra. In the second place, I will try to explain how these new reflections may alter the common image of occasione. In the conclusions, I will try to figure out why Machiavelli changed his vision of this concept.