This talk from Real World Crypto (RWC) 2025 explores the complex relationship between end-to-end encryption and artificial intelligence, covering critical aspects of training, processing, disclosure, and consent. Presented by Mallory Knodel as part of the Secure Cloud & File Storage session chaired by Matthew Campagna, discover how these seemingly opposing technologies interact and what implications arise for privacy, security, and user rights. Gain insights into the technical and ethical considerations that security professionals must navigate when implementing AI systems alongside encrypted communications. The presentation offers a structured framework for thinking about these intersecting technologies in an increasingly AI-driven world where privacy protections remain essential.