Aerodynamic drag is a significant force in cycling, especially at speeds above 40 km/h, where it can account for up to 90% of total resistance. Accurate aerodynamic assessment is essential for optimizing cycling performance through equipment and positional adjustments. However, traditional wind tunnel testing uses static models that fail to replicate the dynamic nature of actual cycling, limiting their ability to investigate biomechanical or physiological factors. This study quantifies the variability introduced by cyclists' repositioning during wind tunnel tests, compares it to drag differences from equipment changes, and evaluates the effectiveness of a real-time feedback system in reducing this variability. The study involved three phases: baseline helmet testing on a static mannequin, development of a position-tracking system, and wind tunnel testing with one amateur and one advanced cyclist. Differences in drag area (CDA) between aero-helmets were around 0.0032 m². Repositioning variability without feedback ranged from 0.003 m² to 0.072 m² for the amateur cyclist and from 0 m² to 0.020 m² for the advanced cyclist. Feedback reduced the amateur cyclist’s variability to 0.005 m² to 0.027 m², comparable to the advanced cyclist. However, feedback had limited effect on the advanced cyclist, with a drag variability of 0 m² to 0.013 m². These findings suggest that repositioning errors can overshadow aerodynamic gains from equipment, particularly for less experienced cyclists. While feedback helps reduce these errors, improved testing methods are needed to fully account for rider variability and optimize performance.