Conservation biology and ecology (as well as our eyes and ears) tell us that nature is in a constant state of flux. Yet, models of land conservation focus on preserving the present state of land in perpetuity. Legal concepts that center on the status quo turn a blind eye to the fact that nature is ever-changing. This conflict is illustrated by examining both traditional property servitudes and conservation easements. These restrictions on private land often explicitly state that they are preserving today’s landscape in perpetuity. This chapter explores the inherent conflict between the changing natural world and rigid legal structures, detailing the struggles of applying principles like resiliency thinking and adaptive management to property tools for conservation. It also explores why this disconnect occurs including some discussion of environmental psychology.