Characterizing the terrestrial carbon, water, and energy cycles depends strongly on a capacity to accurately reproduce the spatial and temporal dynamics of land surface evaporation. For this, and many other reasons, monitoring terrestrial evaporation across multiple space and time scales has been an area of focused research for a number of decades. Much of this activity has been supported by developments in satellite remote sensing, which have been leveraged to deliver new process insights, model development and methodological improvements. In this Special Issue, published contributions explored a range of research topics directed towards the enhanced estimation of terrestrial evaporation. Here we summarize these cutting-edge efforts and provide an overview of some of the state-of-the-art approaches for retrieving this key variable. Some perspectives on outstanding challenges, issues, and opportunities are also presented.