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Online retailers increasingly personalize ads in order to cut through the clutter of online advertising, but the effectiveness of ad personalization is questionable. Notwithstanding that when a retailer is trusted, the effectiveness of a personalized ad increases, as the consumer believes that the usefulness of the ad weighs up to the privacy concerns and reactance associated with such an ad. Furthermore, when the website on which the ad is depicted is trusted, the effectiveness of the ad will also increase, as the consumer no longer experiences vulnerability. Still, the simultaneous effect of retailer trust and website trust has not yet been studied. In that regard, this study has demonstrated that trust in the retailer by itself or trust in the website by itself is not sufficient to positively influence the effect of ad personalization on click-through intentions. After conducting a scenario-based online experiment, four generalized ordered logistic models have shown that when trust is high in both the retailer and the website, personalization has a positive effect on click-through intentions. Conversely, when the retailer is trusted but the website is not, ad personalization has a negative effect on click-through intentions and when the retailer is not trusted, ad personalization has no effect on click-through intentions. Thus, before littering the Internet with more pointless personalized ads, practitioners should reflect on the trust consumers have in them and in their ad publishers. Moreover, they should strive to obtain optimal trusting levels in order to maximize their personalized ads’ effectiveness.