Background: Previous research has identified center of mass vertical oscillation and leg stiffness as the most common variables differentiating Natural and Groucho running techniques. The aim was to assess the inter-session reliability and inter-technique sensitivity of synchronized inertial measurement units and contact grids in quantifying kinematic and kinetic differences between Natural and Groucho running techniques. Methods: Eleven physically active and healthy males ran at a speed 50% higher than transition speed. Two sessions for Natural and two for Groucho running were performed, each lasting 1 min. Results: Most variables exhibited a similar inter-session reliability across running techniques, except contact time and center of mass vertical displacement, ranging from moderate to good (ICC = 0.538–0.897). A statistically significant difference between running techniques was found for all variables (p < 0.05), except for contact time and center of mass vertical oscillation (p > 0.05), likely due to inconsistency in reliability depending on the running technique, which may have covered the underlying differences. Conclusions: We can conclude that the combination of synchronized inertial measurement units and contact grids showed potentially acceptable reliability and sufficient sensitivity to recognize and differentiate between Natural and Groucho running techniques. The results may contribute to a broader understanding of the differences between these two running techniques and encourage the increased use of these devices within therapeutic, recreational, and sports running contexts.