Federal legislation, professional standards, and school district initiatives mandate or support the consideration and application of assistive technology (AT) devices and services for students with disabilities. It is not known if practitioners in the field have the knowledge and skills required to successfully implement AT and AT services as intended. This was an exploratory study to describe and compare the level of AT knowledge among special education professionals and related service providers, identify AT training needs, and determine staff perceptions of the availability and effectiveness of AT technical assistance and support within a school system that serves a large number of parents serving in the military. The study was implemented with descriptive and inferential statistical techniques employed through a self-administered web-based questionnaire. Of the 87 professionals randomly selected, 42 participated. Special education professionals indicated a lack of essential skills and knowledge on selected AT knowledge and skill measures and current AT practices do not meet established AT quality indicators. Each professional had AT knowledge specific to their profession, but the quality and depth of the AT knowledge was similarly limited. The findings question the current effectiveness of existing AT training, policy, and supports across professional disciplines. Results suggested this is in part due to a lack of operational device knowledge and skills compounded by uncertainty of district AT procedures and policy for low and high assistive technology. Timely technical support and professional access to AT Lending Libraries were identified as interventions currently working. The results support a growing body of research in the field of AT regarding the lack of knowledge and skills of special education and related service providers. These results have implications for pre-service AT preparation programs, in-service trainings, and district policy and infrastructure support.