A national survey of special education administrators was conducted on current special education teacher trainings, the internal monitoring processes on transition IEPs, and the effect training has on compliance with federal law. In addition, this student researcher examined training and internal monitoring systems to determine if there were any similarities or differences between rural, suburban, and metropolitan school districts. An explanatory sequential mixed methods design gathered survey data from 147 special education administrators from across the U.S. and conducted interviews with 14 participants representing rural, suburban, and metropolitan school districts. When combining survey and interviews data, the results showed that less than 5 hrs of training was provided to secondary special education teachers on writing compliant transition IEPs per year. While results found that internal monitoring systems were in place in the majority of school districts, the fidelity of implementation is not consistent within or between school districts. The continuous improvement of trainings and writing transition IEPs was not found. Overall, the study found that rural, suburban, and metropolitan local education agencies (LEAs) have more similarities than differences in their professional development (PD) systems and internal monitoring systems and similar challenges impacting their school districts’ transition IEP compliance