This study assesses the usefulness of the remote scheduling of regulated deficit irrigation (RDI) in almond based on the maximum daily trunk shrinkage signal intensity (SIMDS). The 2-year experiment was carried out in SE Spain on 12-year-old almond trees (Prunus dulcis (Mill.) D.A. Webb cv. Guara). Four irrigation treatments were established to evaluate soil–plant water status, yield and water productivity: (i) control treatment (CTL), irrigated to satisfy the maximum crop water requirements (ETc), (ii) RDI1 and (iii) RDI2, both established to maintain different target thresholds of SIMDS according to the phenological stage and (iv) farmer treatment (FRM), irrigated by the grower according to his own experience. In 2009 and 2010 strategies 1.3-2.2-1.6 (SIMDS target threshold for each tree development stages II–III, IV and V, respectively) and 1.6-2.8-1.6 were applied in RDI1, respectively, and strategies 1.0-2.8-1.3 and 1.0-3.2-1.0 in RDI2. A supervisory control and data acquisition platform (SCADA) was created to monitor and remotely manage the irrigation scheduling. The obtained results indicate that SIMDS is a suitable parameter for irrigation scheduling throughout the growing season. The greater or lesser accuracy of fit of the measured SIMDS values to the thresholds depended on the phenological stage and the target stress intensity. SIMDS threshold values higher than 2.8, which involve midday stem water potential (Ψstem) values lower than −1.9 MPa, were not suitable for almond irrigation management under our growing conditions. SIMDS-based RDI strategies were able to generate moderate to severe water stress in almond trees, which resulted in seasonal water savings around 50%. RDI strategies proved to be more cost-effective than full irrigation and farmer deficit irrigation treatment given the high price of irrigation water.