This session explores recent work training subject matter experts (SMEs) to develop assessment items using a human-AI hybrid approach. As AI entered the education and assessment space in 2024, we engaged in virtual conferences, examined ethical risks, and designed a cautious plan for integrating AI into K–12 field test item development. Educator SMEs were trained in item writing and AI use, supported by templates, specifications, and prompts. Initial development was tightly managed to establish procedures and ensure quality. Tools included business rules, submission guides, and bias-aware language resources. A second training round supported deeper skill building. The process revealed successes and challenges, helping shape ongoing documentation and improvements. This session offers practical insights for both experienced users and those new to assessment, with reflections on process design, implementation, and opportunities for refinement.