In response to ever-growing material damages caused by floods over the last two centuries, societies have sought techniques and methods to prevent, minimize, or at least mitigate the physical and social havoc wreaked by such events. It was not until the middle of the nineteenth century, however, that insurance was added to the toolbox of flood management practices. In the United States, despite the large number of physical flood protection devices such as levees, floodwalls, etc., the amount of flood damage continued to increase in the late nineteenth and twentieth centuries. As a response to these developments, the National Flood Insurance Program (NFIP) was created by Congress in 1968. This article sheds light on the conflicted history of the NFIP and especially the challenges resulting from structural deficits, funding issues, the definition of hazard and, more recently, climate change.