Assessment of the health of landscapes, by monitoring their condition over space and time, is needed to better understand the processes for sustaining or, in many cases, repairing them. Remote sensing is a tool that can efficiently identify and assess areas of landscape damage at different scales and help land managers solve specific problems. Remote sensing may appear to be a panacea for all monitoring situations but sometimes the information it provides is not enough by itself. In this paper we give examples of both scenarios—when remote sensing alone is adequate and when it is not. When remotely sensed data alone is not sufficient, monitoring problems can be solved by incorporating additional finer scale data. We use a five-step procedure based on scaling to help land managers answer the question: when is remote sensing data alone not sufficient to underpin the information needs required to achieve a specific management goal?