There are several causes for the failure of empirical models to estimate soil water depletion and to calculate irrigation depths, and the problem is particularly critical in tall, uneven, deficit irrigated (DI) crops in Mediterranean climates. Locally measured indicators that quantify water status are useful for addressing those causes and providing feed-back information for improving the adequacy of simple models. Because of their high aerodynamic resistance, the canopy conductance of woody crops is an important factor in determining evapotranspiration (ET), and accurate stress coefficient (Ks) values are needed to quantify the impact of stomatal closure on ET. A brief overview of basic general principles for irrigation scheduling is presented with emphasis on DI applications that require Ks modelling. The limitations of existing technology related to scheduling of woody crops are discussed, including the shortcomings of plant-based approaches. In relation to soil water deficit and/or predawn leaf water potential, several woody crop Ks functions are presented in a secondary analysis. Whenever the total and readily available water data were available, a simple Ks model was tested. The ultimate aim of this discussion is to illustrate the central concept: that a combination of simple ET models and water stress indicators is required for scheduling irrigation of deep-rooted woody crops.