This single-site case study describes the outcomes and lessons learned from the implementation of a technology professional development initiative aimed at helping three special education teachers from an urban elementary school learn how to infuse technology in their content literacy instruction. Three types of qualitative data were collected: (a) researcher's anecdotal notes during the professional learning sessions; (b) teachers' reflection blog entries; and (c) student artifacts (i.e., digital exit tickets, student work samples). The impact of the technology professional development on teachers' self-efficacy beliefs and Technological Pedagogical Content Knowledge for content literacy instruction, changes in teachers' content literacy instructional and assessment practices, and the influence of teachers' technology professional development on the content literacy learning of students with disabilities are discussed. Recommendations for future professional development programs focused on technology are offered. This study has important implications for urban, high-needs students who need to have equitable access to 21st century digital literacy skills across the content areas in order for them to become college and career ready.