The ancient Greeks had a name for the joy as well as the sorrow of an occasion that suddenly presents itself, but disappears just as swiftly: kairos, or in Latin occasio. Using the Mantua grisaille as starting point and leading motif, Barbara Baert guides us in her own intriguing way through the history of the representation of this figure in art. How did the archaic Greek Kairos model survive in the Quattrocento? Which appearances did Kairos take on along the way and how can we explain his mutations? The author shows us how the semantic and rhetorical expansion of the concept kairos/occasio brought about gender switches and conflations with other personifications of time and fate. Grasping the lock of hair of Kairos/Occasio, spinning the wheel of fortune of Tyche/Fortuna, acting as the mast of the ship and holding the billowing sails, she steers us through depictions of the motionlessness of the moment throughout history before dropping anchor in the fascinating vocabulary of Aby Warburg. During this journey, she invites us to go offshore looking for a new critical moment that presents itself as a powerful opening of possibilities.