Land degradation and desertification has been ranked as a major environmental and social issue for the coming decades. Thus, the observation and early detection of degradation is a primary objective for a number of scientific and policy organizations, with remote sensing methods being a candidate choice for the development of monitoring systems. This paper reviews the statistical and ecological frameworks of assessing land degradation and desertification using vegetation index data. The development of multi-temporal analysis as a desertification assessment technique is reviewed, with a focus on how current practice has been shaped by controversy and dispute within the literature. The statistical techniques commonly employed are examined from both a statistical as well as an ecological point of view, and recommendations are made for future research directions. The scientific requirements for degradation and desertification monitoring systems identified here are: (I) the validation of methodologies in a robust and comparable manner; and (II) the detection of degradation at minor intensities and magnitudes. It is also established that the multi-temporal analysis of vegetation index data can provide a sophisticated measure of ecosystem health and variation, and that, over the last 30 years, considerable progress has been made in the respective research.