The dream of unbroken enclosure is personified, among other, in the endless proliferation of climate-controlled interiors and gleaming architectural facades that mark the neoliberal city. Indeed, the contemporary moment is increasingly characterised by stark divisions between various insides and outsides. This talk, drawing on counter-examples from critical art and design, advocates for practices that—rather than giving shaping to the new or the tightly sealed—instead foreground leakage, in the process serving as sensors of the present in its volatile complexity.