The PlantEye multispectral scanner is an optoelectrical sensor automatically applied to a mechatronic platform that allows the non-destructive, accurate, and high-throughput detection of morphological and physiological plant parameters. In this study, we describe how the advanced phenotyping platform precisely assesses changes in plant architecture and growth parameters of wild rocket salad (Diplotaxis tenuifolia L. [DC.]) under drought stress conditions. Four different irrigation supply levels from moderate to severe, required to keep 100, 70, 50, and 30% of the water-holding capacity, were adopted. Growth rate and plant architecture were recorded through the digital measure of biomass, leaf area, Canopy Light Penetration Depth, five convex hull traits, plant height, Surface Angle Average, and Voxel Volume Total. Vegetation color assessments included hue, lightness, and saturation. Vegetation and senescence indices were calculated from canopy reflectance in the red (620–645 nm), green (530–540 nm), blue (peak wavelength 460–485 nm), near-infrared (820–850 nm), and 3D laser (940 nm) ranges. The temperature, relative humidity, and solar radiation of the environment were also recorded. Overall, morphological parameters, color, multispectral data, and vegetation indices provided over 7200 data points through daily scans over three weeks of cultivation. Although a general decrease in growth parameters with increasing stress severity was observed, plants were able to maintain the same morpho-physiological performances as the control during the early growth stages, keeping both 70% and 50% of the total water-holding capacity. Among indices, the Normalized Differential Vegetation Index (NDVI) contributed the most to the differentiation between different stress levels during the cultivation cycle. Across the 3 weeks of growth, statistically significant differences were observed for all traits except for the Saturation Average. Comparisons with respect to the control highlighted the strong impact of drought stress on morphological plant traits. This study provided meaningful insights into the health status of wild rocket salad under increasing drought stress.