The rapid development of Generative Artificial Intelligence (GenAI) is transforming retail chatbots into sophisticated conversational agents that redefine the customer experience across the entire journey. This entry explores the fundamental tension between the opportunities for enhanced personalization and the critical challenges hindering adoption, including privacy concerns, algorithmic bias, and implementation barriers. By integrating insights from marketing and information systems literature, the analysis provides a conceptual foundation for navigating these trade-offs to create more adaptive, effective, and ethically responsible customer experiences in retail.