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Online behavioral advertising, and the associated tracking paraphernalia, poses a real privacy threat. Unfortunately, existing privacy-enhancing tools are not always effective against online advertising and tracking. We propose HARPO, a principled learning-based approach to subvert online behavioral advertising through obfuscation. HARPO uses reinforcement learning to adaptively interleave real page visits with fake pages to distort a tracker’s view of a user’s browsing profile. We evaluate HARPO against real-world user profiling and ad targeting models used for online behavioral advertising. The results show that HARPO improves privacy by triggering more than 40% incorrect interest segments and 6×higher bid values. HARPO outperforms existing obfuscation tools by as much as 16×for the same overhead. HARPO is also able to achieve better stealthiness to adversarial detection than existing obfuscation tools. HARPO meaningfully advances the state-of-the-art in leveraging obfuscation to subvert online behavioral advertising.