Digital media is becoming increasingly prevalent in households and classroom settings lowering the age of first exposure to technology; however, little is known about how children experience digital media and how their experiences relate to learning and social engagement. In this case study, we followed a 28-month-old boy in a naturalistic setting for 5 weeks, videotaping the process of his interactions with the iPad. Using a combination of video coding, screen recordings, and a formal academic assessment we evaluated the effects of digital media on specific learning outcomes, child affective states associated with gains in digital literacy, and the role of social interaction in the process of digital media exposure. We found that the number of errors predicted a significant amount of the variance in the child's levels of frustration, attentiveness, help-seeking behaviors, and persistence. Two main types of affect, confusion and attentiveness, predicted gains in his iPad proficiency, providing important insights into the role of emotions in digital learning. With increased levels of iPad proficiency, we observed an inconsistent pattern of child social engagement. This study is the first, to our knowledge, to use a combination of qualitative observation data, standardized assessment, and quantitative analysis of a child's behavior in the process of digital literacy learning.