Current Japanese youth are constantly connected to the Internet and using digital devices, but predominantly for social media and entertainment. According to literature on the Japanese digital native, tertiary students do not—and cannot—use technology with any reasonable fluency, but the likely reasons are rarely addressed. To fill the gap in the literature, this study, by employing a case study methodology, explores students’ experience with technology for English learning through the introduction of digital tools. First-year Japanese university students in an Academic English Program (AEP) were introduced to a variety of easily available digital tools. The instruction was administered online, and each tool was accompanied by a task directly related to classwork. Both quantitative and qualitative data were collected in the form of a pre-course Computer Literacy Survey, a post-course open-ended Reflection Activity survey, and interviews. The qualitative data was reviewed drawing on the Technology Acceptance Model (TAM) and its educational variants as an analytical framework. Educational, social, and cultural factors were also examined to help identify underlying factors that would influence students’ perceptions. The results suggest that the subjects’ lack of awareness of, and experience with, the use of technology for learning are the fundamental causes of their perceptions of initial difficulty. Based on these findings, this study proposes a possible technology integration model that enhances digital literacy for more effective language learning in the context of Japanese education.