The United States Supreme Court's decision in Citizens United v. FEC challenged fundamental notions of free speech jurisprudence. While many commentators have focused on the decision's implications for corporate speech, this Comment examines whether the new First Amendment paradigm announced in Citizens United will challenge current speech restrictions on churches and other entities organized under § 501(c)(3). Not only does this Comment propose that such restrictions could potentially be invalidated based on the Court's reasoning in Citizens United, but also that practical factors relating to compliance and enforcement problems inherent in § 501(c)(3) indicate the ban should be amended. This Comment concludes by offering a proposed change to § 501(c)(3)'s politicking ban that would allow a § 501(c)(3) organization to engage in “some” amount of politicking, as long as it was not a substantial part of the organization's overall charitable activity.