Scholars, often drawing from and expanding on Michel Foucault’s 2004 Security, Territory, Population, have focused on issues of security and insecurity, sometimes providing a deep history for the contemporary security state, sometimes exploring the role of security and insecurity in human existence as such. As the meeting of the International Conference on Romanticism’s “Romantic (In)Security” demonstrated, these issues helped define our period as well. In this keynote, we sought to step away from an analysis of security apparatuses and the insecurities they can create to explore how insecurity might be reconceived as a moment of fluidity, of openness, of an acceptance of the freedom to be found in an absence of clear security. Noting that Mary Shelley and Percy Shelley themselves experienced intensely insecure lives, we read four of their key works—Frankenstein and The Last Man, Prometheus Unbound and The Cenci—as profound explorations of the power of insecurity. While figures such as Victor Frankenstein and Jupiter long for a total security that is revealed to be oppressive, others such as Lionel Verney and Beatrice Cenci find in insecurity a way beyond totalizing limits towards freedom.