As generative and agentic AI systems move from prototypes to production, builders must balance innovation with trust, safety, and compliance. This talk explores the unique evaluation and monitoring challenges of next-generation AI, with healthcare as a case study of one of the most regulated domains: Evaluation gaps: why conventional benchmarks miss multi-step reasoning, tool use, and domain-specific workflows—and how contamination and fragile metrics distort results. Bias and safety: demographic bias, hallucinations, and unsafe autonomy that trigger regulatory, legal, and contractual obligations for fairness and safety assessments. Continuous monitoring: practical MLOps strategies for drift detection, risk scoring, and compliance auditing in deployed systems. Tools and standards: open-source libraries like LangTest and HELM, new stress-test and red teaming datasets, and emerging guidance from NIST, CHAI, and ISO. While the examples draw heavily from healthcare, the lessons are broadly applicable to anyone building and deploying generative or agentic AI systems in highly regulated industries where safety, fairness, and compliance are paramount.