The present research examines how brand personality and regulatory focus (promotion vs. prevention) interplay in affecting advertising message persuasiveness. In Experiment 1, the moderating role of brand personality with respect to regulatory focus is tested. The results show that a promotion-framed advertising message is more persuasive for a fictitious exciting brand than is a prevention-framed message, whereas a prevention-framed (vs. promotion-framed) message is more effective for a fictitious competent brand. To replicate Experiment 1 and further test the hypothesis, in Experiment 2, two real brands representing two additional brand personality dimensions (sophistication vs. sincerity) are tested and the influence of individuals’ self-construal level is controlled. The findings reveal that individuals exposed to the sophisticated brand show a more positive attitude when the brand message is promotion framed. By contrast, individuals exposed to the sincere brand react more favorably when the brand is presented with a prevention-framed advertising message.