PurposeThe research aims to investigate how individuals can be persuaded to make purchases through repeated and personalized messages. Specifically, the study proposes a framework of the potential benefits and risks of the online behavioral and data-driven digital advertising (OBA), which can help researchers and practitioners to better understand shopping behavior in the online retailing setting. In addition, the research focuses on the role of privacy concerns in affecting avoidance or adoption of OBA.Design/methodology/approachThe authors apply a structural equation modeling (SEM) approach with partial least square (PLS) regression method to test the research hypotheses through data coming from a structured questionnaire.FindingsOBA is a controversial type of advertising that activates opposing reactions on consumers' perspective. Specifically, acceptance of the OBA is positively related to relevance, usefulness and credibility of the personalized advertisements, while the intention to avoid personalized ads is strictly related to the privacy concerns. Consequently, OBA acceptance and avoidance affected the click intention on the ad and the behavioral intention that are decisive for the success of data-driven digital advertising.Originality/valuePrior research came up with complex theoretical frameworks that explain antecedents of OBA focusing only on ethical issues in marketing, on the effectiveness of a single OBA campaign or on how to create a successful advertising campaign. However, no study focuses on the intended or actual behavior of shoppers. Specifically, filling the gap in the existing literature, our research applies an SEM approach to identify both benefits and risks and the antecedents of the actual behavior of individuals in terms of actual purchases promoted by OBA.