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Illicit website owners frequently rely on traffic distribution systems (TDSs) operated by less-than-scrupulous advertising networks to acquire user traffic. While researchers have described a number of case studies on various TDSs or the businesses they serve, we still lack an understanding of how users are differentiated in these ecosystems, how different illicit activities frequently leverage the same advertisement networks and, subsequently, the same malicious advertisers. We design ODIN (Observatory of Dynamic Illicit ad Networks), the first system to study cloaking, user differentiation and business integration at the same time in four different types of traffic sources: typosquatting, copyright-infringing movie streaming, ad-based URL shortening, and illicit online pharmacy websites. ODIN performed 874,494 scrapes over two months (June 19, 2019–August 24, 2019), posing as six different types of users (e.g., mobile, desktop, and crawler) and accumulating over 2TB of data. We observed 81% more malicious pages compared to using only the best performing crawl profile by itself. Three of the traffic sources we study redirect users to the same traffic broker domain names up to 44% of the time and all of them often expose users to the same malicious advertisers. Our experiments show that novel cloaking techniques could decrease by half the number of malicious pages observed. Worryingly, popular blacklists do not just suffer from the lack of coverage and delayed detection, but miss the vast majority of malicious pages targeting mobile users. We use these findings to design a classifier, which can make precise predictions about the likelihood of a user being redirected to a malicious advertiser.