As technology spaces are increasingly envisioned as learning spaces, their role in "people shaping" especially in light of the advent of MOOCs, online gaming and social media sites, is more closely being observed. This article starts from the assumption that learning and identity construction are inextricably intertwined, regardless of the spaces that such learning takes place. The paper has two aims: 1) to establish the importance of discussions on the interconnectedness of learning, technology and identity construction, and 2) to report on two studies that we conducted in Chile in the context of an EFL teacher training program to support that discussion. One of our studies involved a 16-month inquiry into the influences of a guided reading program supported by e-readers on the evolving teacher identities and literacy skills of a group of 10 pre-service teachers. These individuals evidenced limited cultural capital in an academic setting, an issue that threatened their future effectiveness as teachers. The second study was student-conceived and conducted in the same context. This latter study sought to determine the influence of peer tutoring, made available partly through a social media site (SMS), on the identities and investment in learning of 12 first-year students in the pedagogy program. These incoming students were struggling with imagining themselves as future teachers. Both studies draw on ethnographic tools within the qualitative research paradigm. These tools help to uncover the subtle yet significant ways that collaborative meaning-making made possible with digital tools served to create conditions for the individuals in both studies to transform their identities from marginalized in these contexts to recognizing their own symbolic resources and value in terms of their potential as future effective teachers. In both studies, we frame our understanding and analysis on social cultural theories to help explain the kinds of identity negotiation and changes in investment in learning that the technology tools supported over the research period among these pre-service teachers.