Retaining teachers and accessing professional development have been long-standing struggles for rural school districts, particularly with respect to teachers with special education endorsements. This study examined the effect of asynchronous online professional development in secondary special education and transition for 86 rural special education teachers. In addition, the study compared results of teachers in rural and non-rural settings. Results indicated that rural special education teachers who participated in the online professional development gained knowledge, increased personal capacity to apply research-based practices, and implemented research-based transition practices within their classrooms. Furthermore, participants developed meaningful, collaborative relationships with rural colleagues across the country. While rural and non-rural educators both experienced gains as a result of the professional development, rural educators initially rated their competency in providing transition services much lower than their non-rural peers; however, both groups rated their competency at the same levels at the conclusion of the online professional development.