Fundamental to career-changers’ successful transition into teaching is the design and delivery of post-graduate initial teacher education (ITE) programs. Career-changers enter teaching eager to share applied knowledge from prior occupations; however, support during ITE to facilitate the inclusion of these skills into teaching is often lacking. This study explored this phenomenon from a technology perspective and presents the outcomes of a cross-case analysis of four pre-service career-changers from an Australian university during ITE. Results indicated career-changers perceived their capacity to link existing technology skills to curricula depended on modelling and mentoring of technology integration during ITE subjects and school placements. School cultures combined with IT infrastructures also reportedly impacted technology practice. Recommendations to better support career-changers during ITE are discussed.