Habitat corridors can be essential for persistence of wildlife populations in fragmented landscapes. Although much research has focused on identifying species and places critical for conservation action, the conservation literature contains surprisingly few examples of corridors that actually have been protected and so provides little guidance for moving from planning through implementation. We examined a case study from southern California that combines monitoring of radio-collared mountain lions (Puma concolor) with an assessment of land-protection efforts to illustrate lessons learned while attempting to maintain ecological connectivity in a rapidly urbanizing landscape. As in many places, conservation scientists have provided science-based maps of where conservation efforts should focus. But implementing corridors is a business decision based not solely on ecological information but also on cost, opportunity cost, investment risk, and other feasibility considerations. Here, the type and pattern of development is such that key connections will be lost unless they are explicitly protected. Keeping pace with conversion, however, has been difficult, especially because conservation efforts have been limited to traditional parcel-by-parcel land-protection techniques. The challenges of and trade-offs in implementation make it clear that in southern California, connectivity cannot be bought one parcel at a time. Effective land-use plans and policies that incorporate conservation principles, such as California's Natural Communities Conservation Planning program, are needed to support the retention of landscape permeability. Lessons from this study have broad application, especially as a precautionary tale for places where such extensive and intensive development has not yet occurred. Given how limiting resources are for biodiversity conservation, conservationists must be disciplined about where and how they attempt corridor protection: in rapidly fragmenting landscapes, the opportunity for success can be surprisingly fleeting.