Technology is everywhere in the field of special education. Most special educators use technology in assistive and instructional roles on a daily basis to support the individualized needs of students with disabilities (Okolo & Bouck, 2007). This includes the use of technology in assistive (Edyburn, 2008) and instructional roles (Kennedy & Wexler, in press), depending on the individualized need of the student with a disability. A large portion of university faculty members use technology in one form or another to help convey content and provide engaging learning opportunities to teacher candidates and in-service educators (Kennedy, Hart, & Kellems, 2011; Ludlow & Duff, 2007). Also, technology can provide a pathway for initial training and ongoing professional development to people who live and work in rural or secluded areas through distance education and other technology-based supports such as e-mentoring or bug-in-the-ear coaching (e.g., Jung, Galyon-Keramidas, Collins, & Ludlow, 2006; Rock et al., 2009). In this chapter we present and discuss evidence related to how practitioners and teacher educators (struggle to) utilize technology in their respective roles.