We know that work is recognized as a central component of life for individuals with and without disabilities. It yields many physical and psychological benefits to the individual while simultaneously contributing numerous benefits to society. Lawmakers have enacted a plethora of laws designed to prevent discrimination, provide incentives for employers to hire individuals with disabilities, and facilitate job training/career preparation. Assistive technology figures prominently in disability employment law as a critical strategy for gaining access and supporting employment and upward mobility in the workplace. However, little systematic effort has been devoted to examining assistive technology use and outcomes as they relate to the employment of individuals with disabilities. The purpose of this article is to articulate a series of issues that permeate assistive technology outcome measurement in employment settings and subsequently affect the use of research knowledge for federal and state policymakers. For each issue, the authors pose three questions for critical analysis: Does the law compel the provision of assistive technology? Does outcome data play any part in the operation of the law? When, it does, what kind of data would be useful to collect and where could it be found? Finally, the authors provide a brief glimpse of the current and future research efforts concerning the RSA-911 database. The recent database summaries exemplify the importance of such a national data collection system for informing federal policy, particularly concerning the contributions of assistive technology device use and services on improving the employment of individuals with disabilities.