Winter wheat (Triticum aestivum L.) is essential to maintain food security for a large proportion of the world's population. With increased risk from abiotic stresses due to climate variability, it is imperative to understand and minimize the negative impact of these stressors, including high night temperature (HNT). Both globally and at regional scales, a differential rate of increase in day and night temperature is observed, wherein night temperatures are increasing at a higher pace and the trend is projected to continue into the future. Previous studies using controlled environment facilities and small field-based removable chambers have shown that post-anthesis HNT stress can induce a significant reduction in wheat grain yield. A prototype was previously developed by utilizing field-based tents allowing for simultaneous phenotyping of popular winter wheat varieties from US Midwest and advanced breeding lines. Hence, the objectives of the study were to (i) design and build a new field-based infrastructure and test and validate the uniformity of HNT stress application on a scaled-up version of the prototype (ii) improve and develop a more sophisticated cyber-physical system to sense and impose post-anthesis HNT stress uniformly through physiological maturity within the scaled-up tents; and (iii) determine the impact of HNT stress during grain filling on the agronomic and grain quality parameters including starch and protein concentration. The system imposed a consistent post-anthesis HNT stress of + 3.8 °C until maturity and maintained uniform distribution of stress which was confirmed by (i) 0.23 °C temperature differential between an array of sensors within the tents and (ii) statistically similar performance of a common check replicated multiple times in each tent. On average, a reduction in grain-filling duration by 3.33 days, kernel weight by 1.25% per °C, grain number by 2.36% per °C and yield by 3.58% per °C increase in night temperature was documented. HNT stress induced a significant reduction in starch concentration indicating disturbed carbon balance. The pilot field-based facility integrated with a robust cyber-physical system provides a timely breakthrough for evaluating HNT stress impact on large diversity panels to enhance HNT stress tolerance across field crops. The flexibility of the cyber-physical system and movement capabilities of the field-based infrastructure allows this methodology to be adaptable to different crops.