This Article examines how the IRS engendered the continuing controversy over claims of misapplication of the Tax Code targeting Tea Party groups applying for tax-exempt status. By surveying the Tax Code, legislative history, and reports in light of the scandal, this Article proposes these challenges actually stem from a fundamental IRS failure-the failure to issue meaningful administrative guidance on key definitions such as social welfare and permissible election campaign activities of Section 501(c)(4) organizations. As such, this Article faults the long-term laxity of the IRS and its failure to resolve statutory ambiguities for creating conditions conducive to arbitrary enforcement and the de facto restructuring of tax-exempt organizations under Section 501(c)(4) as permissible campaign-finance vehicles. Further, this Article discusses how the United States Supreme Court contributed to the shift of utilizing Section 501(c)(4) organizations for furthering political funding goals by analyzing the Court’s decision in the landmark case, Citizens United v. Federal Election Commission. This Article foreshadows new challenges navigating laws regulating tax and campaign finance by highlighting the impact of the lingering effect of the Court’s decisions to adhere to a limited agency role in election law and to protect political free speech.