This paper presents a tailored pedagogical approach to digital heritage documentation in contexts where heritage is under threat. It was developed during the July–August 2024 UNESCO/ICOMOS mission to Kyiv, Ukraine, within the UNESCO/Japan Funds-in-Trust project “Support for Ukraine in Culture and Education through UNESCO / Emergency response for World Heritage and cultural property: damage assessment and protection,” in relation to the UNESCO World Heritage property “Kyiv: Saint-Sophia Cathedral and Related Monastic Buildings, Kyiv-Pechersk Lavra.” The mission focused on the Metropolitan’s Residence and the Bell Tower of the Saint-Sophia Cathedral Complex. In parallel with the production of documentation for emergency preparedness and future conservation assessment, the mission implemented a dedicated capacity-building programme for the staff of the National Conservation Area “Sophia of Kyiv.” The paper discusses five interconnected components of this training programme: preparation before the mission, structure and content of the sessions, training activities and didactic material, learning outcomes and targeted competencies, and adaptive responses to a conflict-affected environment. The case study shows that integrating training into an active documentation workflow can strengthen both the immediate value of the records produced and the longer-term capacity of local professionals to support conservation, monitoring, and risk preparedness at World Heritage sites under threat.