Although recent studies have highlighted young people with intellectual disabilities’ (ID) difficulties with reading and writing, it is not well-know how these skills are used in their daily life and, even less, regarding their digital literacy. Consequently, the aim of this study was to describe the daily use of digital literacy among adolescents, aged 15–21 years, with ID. An additional aim was to identify the factors that facilitated or hindered the various reading and writing practices beyond the classroom context, including home and other familiar spaces like the grocery store. To do so, the digital literacy practices of two adolescents were identified through an ethnographic multi-case study by using creative methods to generate qualitative data. Through Sen’s and Nussbaum’s capability frameworks, it was found that these two young people employed digital literacy through applications on mobile phones and electronic tablets. They developed different capabilities and functionings, particularly “affiliation” and “senses, imagination, and thoughts”. The discussion section of this study focuses on how daily- and school-based digital literacy usages can be bridged to support young people with IDs’ learning and engagement at school.