Joseph Drenth, who is legally blind, faced an untenable choice: vote by mail and sacrifice the ability to cast a private and independent vote, or continue to vote privately and independently at a polling location and sacrifice the health and safety of himself and his family due to the COVID-19 pandemic?1 Fortunately, a preliminary injunction ordering the state to implement a remote accessible vote-by-mail system made such a choice unnecessary for Mr. Drenth. Unfortunately, voters with disabilities in many other jurisdictions throughout the country were not so lucky. Even as the threat of COVID-19 hopefully moves to our rearview mirrors, Mr. Drenth’s successful lawsuit highlighted a critical but underutilized legal tool for ensuring that voters with disabilities are afforded an equal voting experience—including the ability to cast a private and independent ballot—as compared to other voters. This article proceeds in three parts. Part I summarize the history of voting with a disability and outlines the main federal statutes related to voting rights for individuals with disabilities. Part II explains how federal courts initially narrowed the guarantee of the ADA and the Rehab Act to mere technical equality in a way that denied equal dignity and treatment when voting with a disability. It then analyzes a more recent line of cases that backs away from this early case law to expand the reach of the ADA and Rehab Act to also ensure substantive equality and a fuller, more robust right to vote with a disability. Part III then speculates about broader adherence to a mandate of substantive equality throughout the federal judiciary.