In a post-digital world, young people face new challenges and demands of their technology practice as they complete secondary education and transition into higher education contexts. Such challenges have been intensified by the widespread disruption of the COVID-19 pandemic. The higher education sector has responded to the ongoing pandemic by shifting to variations of remote teaching, where students engage with combinations of online/face-to-face and synchronous/asynchronous modes of learning. The aim of this study was to explore the technology practice of young people across their post-school transition to higher education. This is important to investigate because this transition is complex, characterised by uncertainty and places increased demands on young people in terms of their technology practice and digital literacy. We employed a mixed method design to capture in-depth insights into the technology practices of young people across this transition. Participants were recruited from 100-level Education, Nursing and Physics subjects in their first semester of study in 2020. To capture the complexity of students’ transition, the study was conducted at two points in time: in the first weeks of students’ transition to university study (Phase 1); and at the end of their first session (Phase 2). Phase 1 included a questionnaire of over 250 first-year students that captured quantitative data about students’ current digital literacy and open-ended responses about student’s preparedness and understanding of the digital literacy demands of university. Following this, 15 case study students were randomly selected across the three disciplines to participate in an interview. Phase 2 included follow up interviews with case participants at the end of session. Interview questions were informed by the study’s theoretical framework, the theory of practice (Bourdieu, 1977). The questions were designed to explore young people’s regular technology practice, their experiences of transition and the role of their technology practice and digital literacy across their transition. The findings illustrate the real and complex challenges of transition to university during the COVID-19 pandemic, including the increased demands on digital literacy and self-regulation created by emergency remote learning. Furthermore, young people were able to leverage their existing technology practice, in varied ways, to support their engagement across their initial transition. An understanding of the demands on young people as they transition to new and varied blended learning environments in higher education is important for educators who wish to reimagine teaching and learning that better supports all young people in complex and uncertain times.