Canopy temperature (CT) is often interpreted as representing leaf activity traits such as photosynthetic rates, gas exchange rates, or stomatal conductance. This interpretation is based on the observation that leaf activity traits correlate with transpiration which affects leaf temperature. Accordingly, CT measurements may provide a basis for high throughput assessments of the productivity of wheat canopies during early grain filling, which would allow distinguishing functional from dysfunctional stay-green. However, whereas the usefulness of CT as a fast surrogate measure of sustained vigor under soil drying is well established, its potential to quantify leaf activity traits under high-yielding conditions is less clear. To better understand sensitivity limits of CT measurements under high yielding conditions, we generated within-genotype variability in stay-green functionality by means of differential short-term pre-anthesis canopy shading that modified the sink:source balance. We quantified the effects of these modifications on stay-green properties through a combination of gold standard physiological measurements of leaf activity and newly developed methods for organ-level senescence monitoring based on timeseries of high-resolution imagery and deep-learning-based semantic image segmentation. In parallel, we monitored CT by means of a pole-mounted thermal camera that delivered continuous, ultra-high temporal resolution CT data. Our results show that differences in stay-green functionality translate into measurable differences in CT in the absence of major confounding factors. Differences amounted to approximately 0.8°C and 1.5°C for a very high-yielding source-limited genotype, and a medium-yielding sink-limited genotype, respectively. The gradual nature of the effects of shading on CT during the stay-green phase underscore the importance of a high measurement frequency and a time-integrated analysis of CT, whilst modest effect sizes confirm the importance of restricting screenings to a limited range of morphological and phenological diversity.