Modern viticulture faces significant challenges including climate change and increasing crop diseases, necessitating sustainable solutions to reduce fungicide use and mitigate soil health risks, particularly from copper accumulation. Advances in plant phenomics are essential for evaluating and tracking phenotypic traits under environmental stress, aiding in selecting resilient vine varieties. However, current methods are limited, hindering effective integration with genomic data for breeding purposes. Remote sensing technologies provide efficient, non-destructive methods for measuring biophysical and biochemical traits of plants, offering detailed insights into their physiological and nutritional state, surpassing traditional methods. Smart phenotyping is essential for selecting crop varieties with desired traits, such as pathogen-resilient vine varieties, tolerant to altered soil fertility including copper toxicity. Identifying plants with typical copper toxicity symptoms under high soil copper levels is straightforward, but it becomes complex with supra-optimal, already toxic, copper levels common in vineyard soils. This can induce multiple stress responses and interferes with nutrient acquisition, leading to ambiguous visual symptoms. Characterizing resilience to copper toxicity in vine plants via smart phenotyping is feasible by relating smart data with physiological assessments, supported by trained professionals who can identify primary stressors. However, complexities increase with more data sources and uncertainties in symptom interpretations. This suggests that artificial intelligence could be valuable in enhancing decision support in viticulture. While smart technologies, powered by artificial intelligence, provide significant benefits in evaluating traits and response times, the uncertainties in interpreting complex symptoms (e.g., copper toxicity) still highlight the need for human oversight in making final decisions.