This narrative study explored the holistic, interconnected challenges that impact special education practitioners in three cross-categorical (CC) special education junior high classrooms in rural Central Illinois. Participants included three junior high school special education teachers, three special education administrators, and three junior high district principals. Over a period of six weeks, participants were interviewed three times focusing on their changing roles in special education. Results suggest that special education practitioner retention is negatively impacted by restrictive evaluations and growth components, the prevalence and intensity of student behaviors, and scarcity of classroom resources including time, scheduling, and training, as well as the changing roles, increased responsibilities, and perceived lack of support of special education teachers. Results are discussed in terms of implications for special education engagement and professional development, and in terms of the wider systemic implications of support and scheduling. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]