Moving from the architectural intelligence of Northwood School to the intimate, wrist-worn companion systems of Riverside Crest School, iBuddy - My AI Pal explores the delicate and nearly invisible contract forged between human judgment and automated care. Authored as a narrative-driven monograph, this volume investigates localized AI companions, emotional and psychological attachments, crisis protocols, and multi-tiered pedagogical workflows. Designed for secondary students, educators, and researchers alike, it transitions from Alex's personal journey into a robust, working framework of ethical guardrails and human oversight-inviting readers to help design the next phase of human-centered technology.