Special education teachers are expected to integrate assistive technology (AT) for students with disabilities per Individuals with Disabilities Education Act (IDEA). However, the legal mandates do not provide clear guidelines regarding the type, the frequency, and the purpose for which AT can be used and, often, the decision of AT integration is left up to teachers and members of Individualized Educational Plan (IEP) teams who may or may not have complete knowledge of the AT implementation strategies. This research study provides an overview of how teachers of different content areas in a technology-rich self-contained secondary program for students with learning disabilities implemented AT in their daily instruction. Teacher reports and observations reflected discrepancies in how teachers may perceive their teaching with AT and revealed that, in spite of having access to a variety of technologies, there continues to be a focus on using low and medium AT (less complex technology). Specific factors (barriers) that influenced the integration of technology for students with learning disabilities are also investigated and described.