This qualitative study examines how students’ identities are constructed when technology and disability intersect. Understanding how technology constructs the identities of students with invisible special needs such as learning disabilities is critical to determining why students are resistant to, or accepting of, assistive technology pedagogy. The primary source of data for the study was in-depth, phenomenologically based interviewing using structured, open-ended dialogue. Three Ontario secondary schools provided the setting for the study. Participants included five students with learning disabilities who are users of assistive technology, two parents, two teachers, and two assistive technology coaches. A grounded theory methodology was used to permit theoretical categories to emerge from the data. The purpose of the research was to investigate: (a) Is the promise of technology compromised by the visibility of technology support, and how do students who access technology through the Special Equipment Amount (SEA) negotiate any related social dynamic? (b) What does the diagnosis of a learning disability mean to students and their parents? (c) What are the particular experiences and contexts within which students that access technology through SEA are trained? and (d) How do teachers, parents, and trainers see their role in the technology assistance program? The research findings indicated a strong positive association between the variables of awareness, understanding, and acceptance. Participants’ responses revealed: (a) a direct relationship between students’ lack of awareness of having a disability and lack of knowledge regarding why they have a SEA laptop with access to Assistive Technology (AT), (b) a strong connection between students’ awareness and understanding of the diagnosis of LD and their willingness to “own” or accept a disabled identity in order to access necessary supports such as AT, and (c) overall, that awareness, understanding, and acceptance of a LD appeared to significantly impact students’ willingness to happily engage with AT. Beliefs expressed by participants about responses to AT revealed tensions between the promised empowerment of AT and the negative self-perception related to AT use. Students appeared to be unwittingly trapped in a cost-versus-benefit dynamic, such as independence and improved abilities versus inferior status and social labelling. Consistent with the literature on stigma related to invisible disabilities, students in some instances appeared to shoulder the burden associated with the social cost of being perceived as academically inferior. Participants perceived several reasons for lack of engagement and abandonment of SEA equipment, including stigmatized identities, compromised self-esteem, and indifference. Although these reasons prove to be barriers to successful integration and engagement with SEA equipment, in this study, stigma appeared to be the most powerful recurring explanation for AT abandonment