Prior to the 2020 election, lawmakers in several states sought to expand voting rights for individuals with felony convictions, and while this work is important, a large swath of voters who legally never lost the right to vote are still unable to do so because they are detained in jail. These individuals, often detained prior to trial, have the right to vote pursuant to a 1974 Supreme Court ruling in O’Brien v. Skinner. However, despite the clear legal precedent protecting voting rights for those in jail, the right remains unrealized for most incarcerated individuals due to numerous barriers. Some localities, such as the Cook County jail, have taken steps to provide access to voting to those in jail. However, a multi-faceted approach using policy and legal solutions is necessary to address disenfranchisement in jail. This Comment first examines the extent of disenfranchisement in jail by showing that disenfranchisement specifically targets indigent individuals and minorities. It also reveals the specific barriers incarcerated individuals face when trying to vote from jail. Next, this Comment reviews and critiques the existing legal landscape of voting rights for those in jail stemming from the O’Brien case. Finally, this Comment offers potential legal and policy solutions that can redress the rights violations faced by those in jail who are unable to vote.