Wind turbines are eco-friendly energy sources that generate electricity from wind power. Among their various components, gearboxes constitute the most critical loss owing to their longest downtime. To guarantee their durability, a flexible pin was designed based on the original straddle-mounted pin for enhanced tooth load sharing and distribution in the planetary gear set (PGS) of a wind turbine gearbox (WTGB). The improved durability was evaluated by calculating the mesh load factor and face load factor for contact stress and comparing these values with those of the original straddle-mounted pin. The mesh load factor decreased from 1.37 to 1.08, whereas the maximum face load factor decreased slightly, moderating the overall safety factor variation. Furthermore, the structure of the proposed flexible pin model was analyzed and verified that no static failure or interference occurred. Additionally, microgeometry optimization was applied to improve the load distribution. Therefore, it was verified that a flexible pin applied to a single helical-geared PGS, thus far considered impossible, enhances the durability of WTGBs by improving the load sharing and distribution of a PGS. Consequently, the possibility of designing single helical-geared planetary gearboxes with flexible pins to take advantages of both helical gears and flexible pins was shown analytically.