More than half of global water use can be attributed to crop irrigation, and as the human population grows, so will the water requirements of agriculture. Improved irrigation will be critical to mitigating the impact of increased requirements. An ideal irrigation system is informed by measurements of water demand—a combination of water use and water status signals—and delivers water to plants based on this demand. In this review, examples of methods for monitoring water status are reviewed, along with details on stem and trunk water potential measurements. Then, methods for monitoring evapotranspiration (ET), or water use, are described. These methods are broken into coarse- and fine-scale categories, with a 10 m spatial resolution threshold between them. Fourteen crop ET technologies are presented, including examples of a successful estimation of ET in research and field settings, as well as limitations. The focus then shifts to water distribution technologies, with an emphasis on the challenges associated with the development of systems that achieve dynamic single plant resolution. Some attention is given to the process of choosing ET and water status sensing methods as well as water delivery system design given site characteristics and agronomic goals. This review concludes with a short discussion on the future directions of ET research and the importance of translating findings into useful tools for growers.