We subjected rubber coupons to cyclical uniaxial tension to investigate the softening effect, where the primary loading at its initial position was followed by additional unloading and reloading. Less stress was required upon reloading than that required in the previous loading for the same degree of stretch, reached on the first loading. This stress softening is significant when reloading follows virgin loading. The magnitude of stress softening is related to the maximum stretch elastomers can achieve in each cycle. To investigate this phenomenon, rubber coupons were subjected to four cycles of simple tension until the desired stretch was reached. We expected that several tests under the same conditions would provide almost identical results. However, we observed different stress requirements for different degrees of stretch when multiple cycles of the same stretch were performed. For three different experimental tests of the same amount of stretch, we saw huge differences in each cycle of loading-relaxation-reloading, a phenomenon that was more obvious during stress relaxation.