Habitat conservation plans (HCPs) are enabled under section 10(a) of the Endangered Species Act. The substantial increase since 1994 in the number of HCPs has motivated numerous critiques of nearly every aspect of HCPs. These critiques have overlooked several paradoxes that expose fundamental shortcomings of section 10(a) or its implementation. I refer to them as: the Trainwreck Paradox, the Jeopardy Paradox, and the Maximum Mitigation Paradox. The Trainwreck Paradox states that HCPs are needed to avert the listing of species as threatened or endangered, but federal listings are needed to motivate landowners to develop HCPs. The Jeopardy Paradox stems from the vague language of section 10(a) which allows an HCP to reduce the likelihood of a species’ survival and recovery but establishes no objective limit on the magnitude of reduction. The Maximum Mitigation Paradox argues that if a landowner provides maximum mitigation at the onset of an HCP, then there will be no financial resources for adaptive management in the future, but if resources are reserved for adaptive management, then the landowner is not mitigating to the maximum extent practicable as required by section 10(a). The purpose of this article is to explain these paradoxes of HCPs and discuss potential remedies.