This paper examines the evolving participation of instructors and learners in an after-school web page-design course intended to improve technology practices. Defined here as technology fluency, these practices emerge through a highly fluctuating dance among social interactions with others and with the technology. In this digital divide initiative, White suburban high-school boys teach web page design to middle-school-aged African-American youths. Using sociotechnical and cultural sociology theories, this qualitative case study explores the development of technology practices as they evolve through social, technical, and cultural interactions. Attention is given to the transformation of instructor schemata and practices as instructors and learners interact throughout the course. The methodology uses case-study and design-research approaches to analyse observational, video, fieldnote, and e-mail data. The results offer a conceptualization of change as well as the affordances and constraints of that change, and provide insight into the design of emergent technology programmes.