As mobile‐only use has increased over the last decade, research has found that mode of online access (mobile‐only vs. mobile and computer use) is related to digital inequalities. Relying on the literature on affordances and digital inclusion, this study seeks to: (1) examine the effects of mode of access on the number of online activities, over time; and (2) understand how the context of transitioning between modes of access shape how people perceive technologies. We conducted a 3‐year mixed‐methods longitudinal study. First, we ran a two‐wave representative panel survey in Chile (N = 512). People who became hybrid users increased their activities, whereas those who became mobile‐only decreased them. Then, we interviewed a subsample of people who switched mode of access between waves (N = 22). We found that people's relation with devices and their choices evolve over time according to their shifting needs and contexts. These results point to users’ agency and the relevance of the concept of affordances. Thus, we propose the concept of transitional affordances to explain how users’ perceptions, experiences, and ability to compare between mode of access shape their relation, engagement, and perceived affordances of technologies.