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In the ever-evolving landscape of digital experiences, AI-driven personalization has emerged as a pivotal force shaping how users interact with web content. This study conducts a comparative analysis of AI-driven personalization strategies in web content delivery, focusing on user engagement in the United States (USA) and the United Kingdom (UK). The research delves into the nuanced ways in which AI algorithms tailor web content to individual user preferences, examining the impact on user engagement metrics such as time spent on site, click-through rates, and conversion rates. Through a meticulous examination of AI-driven personalization practices employed by web platforms in both regions, this study seeks to identify common trends, regional differentiators, and their implications on user engagement. Key factors considered include the ethical dimensions of personalization, the adaptability of AI algorithms to diverse user behaviors, and the fine balance between customization and privacy concerns. The findings aim to contribute valuable insights to the fields of AI-driven web content delivery, user experience design, and the global discourse on the intersection of technology, personalization, and user engagement.