The technological, pedagogical, and content knowledge (TPACK) framework considers the role of technology in teaching. Although TPACK is grounded in context, one limitation is the lack of understanding about the interactions between particular contexts, knowledge development, and instruction. This qualitative multiple-case study was designed to explore the contextual factors that contribute to teachers' development of technological, pedagogical, and content knowledge and practice. Researchers focused on the Catholic educational environment to develop a more refined understanding of specific, and unique, contextual factors within the TPACK framework. Individual case analysis of interview and observation data pointed toward microlevel, or teacher-centric, factors, including background, attitudes, and personal conceptualization of contemporary education, to be primary influences of the development and use of technological knowledge. Recommendations are made for educators to think about how changes in context influence the distinct overlapping components of the TPACK framework, and accordingly their individual TPACK.