<p>Despite the importance of determining when it is appropriate to recontact digital customers, considering both retargeting effectiveness and privacy concerns, this issue has been underexplored in previous research. Unlike previous retargeting studies that infer decision stages from fragmented actions, we uncover consumers’ purchase concerns from a series of actions in their purchase journey. A randomized field experiment reveals that personalized retargeting, compared to non-personalized retargeting, improves purchase conversion for consumers with product-related concerns (e.g., product fit or price). However, for consumers with privacy concern dominance, it can backfire, decreasing purchase conversion. These findings highlight the importance of integrating retargeting audience and content research by identifying and addressing dominant purchase concerns. Insights from the studies help firms make better choices about whom to retarget and what messages to convey when developing retargeting strategies, resolving the trade-off between retargeting effectiveness and privacy concerns.</p>