This research investigates how brand strategy and technological uncertainty influence the order-of-entry effects for a previous generation pioneer in the successive generation. The findings of our longitudinal experiment reemphasize the importance of continuous pioneering, demonstrating that consumers exhibit a strong preference for a previous generation pioneer's product when it continues to pioneer the successive generation. More importantly, the findings indicate that continuous pioneering with a new brand leads to greater brand preferences when technological uncertainty is high. This is because in that condition, consumers perceive greater innovativeness with a new brand than with the extant one. On the other hand, an extant brand increases consumer brand preferences for a previous generation pioneer's product in the successive generation when technological uncertainty is low. The theoretical and practical implications of the results for understanding and managing pioneering advantage and brand strategy in the multigenerational product markets are discussed.