This talk presents a technical case study of applying agentic AI systems to automate community operations at PyCon DE & PyData, treated as an open-source testbed. The key lesson is simple: AI only works when put on a leash. Reliable results required good architecture, a clear plan, and structured data models — from YAML and Pydantic schemas to reproducible pipelines with GitHub Actions. With that foundation, LLM agents supported logistics, FAQs, video processing, and scheduling; without it, they failed. By contrasting successes and failure modes across different coding agents, the talk demonstrates that robust design, validation, and controlled context are prerequisites for making agentic AI usable in real-world workflows.