Evolving changes in the law and documentation guidelines since the 1990 Americans with Disabilities Act have led to a loosening of the definition of disability, in which relative weaknesses are now interpreted as evidence of a disability. In this paper, after acknowledging my own shortcomings, I trace the evolution of the law and documentation guidelines from the late 1990s to the present. I discuss how this has led to increased pressure from parents and students on evaluating clinicians to diagnose a disorder and confirm that the student has a disability that requires academic accommodations. Rather than recommending effective interventions and compensatory strategies, many stakeholders (parents, students, psychologists, disability support professionals) now seem to preferentially favor provision of accommodations. I conclude by describing how these changes have affected my own practice and make recommendations for best practices for disability documentation.