Online behavioral advertising that tracks user data has witnessed a dramatic increase in popularity. Using Psychological Reactance Theory, this study examines the effects of brand trust and website credibility on responses to behavioral advertising via privacy concerns. A 2 (brand trust: high vs. low) by 2 (website credibility: high vs. low) between-subjects experiment was conducted (N = 424). Results suggest that while brand trust influences purchase intention—as mediated via affective reactance— website credibility only exerts modest effects on the dependent variables. Implications for user perception factors and contextual factors—including ad effectiveness in the digital personalized marketing realm—are discussed.