DraftKings is facing renewed scrutiny over how it may use artificial intelligence and behavioral advertising to reach customers who show signs of chronic or high-risk gambling. The issue, highlighted by the Electronic Frontier Foundation (EFF), centers on the ability of AI systems to analyze user behavior, identify patterns linked to gambling activity, and help platforms deliver more personalized marketing. Critics warn that this kind of targeting could intensify gambling-related harm by directing promotions toward people who may be especially vulnerable, rather than limiting exposure or offering meaningful safeguards. The debate also raises broader questions about whether existing privacy and consumer-protection rules can keep pace with automated profiling in online betting. As sports gambling expands across digital platforms, the DraftKings case illustrates the tension between sophisticated advertising technology, user privacy, and responsible gambling practices. The controversy is likely to fuel further discussion about transparency, consent, and restrictions on algorithmic marketing in the gambling industry.