Introduction: Ski deflection is a performance-relevant factor in alpine skiing and the segmental and temporal curvature characteristics (m−1) along the ski have lately received particular attention. Recently, we introduced a PyzoFlex® ski deflection measurement prototype that demonstrated high reliability and validity in a quasi-static setting. The aim of the present work is to test the performance of an enhanced version of the prototype in a dynamic setting both in a skiing-like bending simulation as well as in a field proof-of-concept measurement. Material and methods: A total of twelve sensor foils were implemented on the upper surface of the ski. The ski sensors were calibrated with an empirical curvature model and then deformed on a programmable bending robot with the following program: 20 times at three different deformation velocities (vslow, vmedium, vfast) with (1) central bending, (2) front bending, (3) back bending, (4) edging left, and (5) edging right. For reliability assessment, pairs of bending cycles (cycle 1 vs. cycle 10 and cycle 10 vs. cycle 20) at vslow, vmedium, and vfast and between pairs of velocity (vslow vs. vmedium and vslow vs. vfast) were evaluated by calculating the change in the mean (CIM), coefficient of variation (CV) and intraclass correlation coefficient (ICC 3.1) with a 95% confidence interval. For validity assessment, the calculated segment-wise mean signals were compared with the values that were determined by 36 infrared markers that were attached to the ski using an optoelectrical measuring system (Qualisys). Results: High reliability was found for pairs of bending cycles (CIM −0.69–0.24%, max CV 0.28%, ICC 3.1 > 0.999) and pairs of velocities (max CIM = 3.03%, max CV = 3.05%, ICC 3.1 = 0.997). The criterion validity based on the Pearson correlation coefficient was r = 0.98. The accuracy (systematic bias) and precision (standard deviation), were −0.003 m−1 and 0.047 m−1, respectively. Conclusions: The proof-of-concept field measurement has shown that the prototype is stable, robust, and waterproof and provides characteristic curvature progressions with plausible values. Combined with the high laboratory-based reliability and validity of the PyzoFlex® prototype, this is a potential candidate for smart ski equipment.