Insider threats are changing. This chapter looks at how Artificial Intelligence (AI) is now part of that risk, not just as a tool misused by people, but as something that can act in unpredictable or harmful ways on its own. To help educators respond to the evolving threat landscape of insider threats, the chapter sets out a practical teaching framework that brings together real-world examples, ethical reflection, and cross-disciplinary teaching. It uses Bloom’s Taxonomy to support progression, helping students move from understanding to action as they explore insider risk in AI-heavy environments. This chapter proposes a four-level model to help differentiate between AI-enabled and AI-entity threats. Each level is supported by real case studies, giving students the chance to connect theory to practice. The aim is to help educators prepare students for a future where the insider is not always a person, and where judgment, reflection, and critical thinking matter as much as technical skills.