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Although the development of college-going skills has been well studied, sociohistorical changes brought about by the introduction of digital technology have created new layers of inquiry that demand further investigation of this phenomenon. This case study examined high school students’ experience in a technology-integrated math class. Data was collected using one-on-one interviews, focus groups, and an open-ended online questionnaire. The participants’ descriptions of their experience in this class provided insights that outlined the daily routines that became more meaningful because of the integration technology and generated new knowledge about how the use of technology supported the growth of college-going skills. Recommendations are provided on values that should guide technology integration in order to ensure successful skill development.