Rural schools experience difficulty in filling teaching positions at higher rates than non-rural schools. Recruiting and retaining teachers are critical in these districts; however, because the term “rural” is variable, a one-size-fits-all response is not possible. Rural communities tend to be geographically remote, have a low critical mass of students with distinct disabilities, and have relatively few resources to provide differential support for students. In this context, special educators may find themselves in circumstances where they operate as general specialists who are responsible for addressing a broad range of student needs without the support of other related service providers (e.g., school psychologists, curriculum specialists, school counselors, speech and language pathologists). Garwood’s article provides a catalyst to consider ecological system factors that affect burnout, attrition, and, as a consequence, instruction, particularly for students with disabilities. In this response, we view this issue from a perspective of rural schools, where the system contexts are varied and directly impact teacher-level variables, such as the ability to implement evidence-based practices (EBPs) with fidelity. Taking a developmental systems approach, we describe what makes rural settings unique and how these characteristics interact with the critical features of EBPs, as well as suggest how preparation and induction programs might better prepare and sustain teachers to adapt instruction to these rural contexts. We conclude with implications for practice and policy.