Health information technologies have become a central fixture in the mental healthcare landscape, but few frameworks exist to guide their adaptation to novel settings. This paper introduces the contextualized technology adaptation process (CTAP) and presents data collected during Phase 1 of its application to measurement feedback system development in school mental health. The CTAP is built on models of human-centered design and implementation science and incorporates repeated mixed methods assessments to guide the design of technologies to ensure high compatibility with a destination setting. CTAP phases include: (1) Contextual evaluation, (2) Evaluation of the unadapted technology, (3) Trialing and evaluation of the adapted technology, (4) Refinement and larger-scale implementation, and (5) Sustainment through ongoing evaluation and system revision. Qualitative findings from school-based practitioner focus groups are presented, which provided information for CTAP Phase 1, contextual evaluation, surrounding education sector clinicians’ workflows, types of technologies currently available, and influences on technology use. Discussion focuses on how findings will inform subsequent CTAP phases, as well as their implications for future technology adaptation across content domains and service sectors.