After major disaster events such as cyclones, floods, and wildfires, insurance companies warn of growing risks vis-à-vis climate change and the corporate bottom line. In response to rising home and contents insurance premiums and a collapse of insurability in some places, headlines proclaim that we are headed for an uninsurable future. Yet, collapses in insurance come in all kinds of shapes and sizes, and in this chapter I examine three: the corporate collapse of a large insurer; the slower-moving collapse in insurability for homes in the Westernised world due to climate risks; and systemic collapse of the modern world and Ulrich Beck’s proposition that the indicator of such an end is the loss of adequate private insurance coverage. My purpose is to illustrate the complex, situational, and processual characteristics of events and circumstances that fall under the term ‘collapse’. A collapse of insurance depends, among other things, on who and where you are and who has the power to tell the story of collapse and lead decision-making and responses. I conclude with a critique of the term ‘transformation’ as a problematic synonym for collapse, one that disappears complexity, inequality, and inequity.