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This Article offers a critical exploration of Day's views on the relationship between the tax system and Catholic social theory. Part I of this Article provides a biographical sketch of Dorothy Day and an overview of the Catholic Worker movement. Part II explores Day's views on taxation, pacifism, and social justice. It attempts to reconcile her belief in wealth redistribution with her nonpayment of federal income taxes and her failure to seek tax-exempt status for the Catholic Worker. Part III examines Day's tax resistance in the context of Catholic social teaching, particularly as that thought was developing during Day's lifetime in the twentieth century. It explains how Day's views on taxation were out of step with the emerging contours of traditional Catholic teaching on tax compliance. Part IV then explores what implications Day's protests might have for better integrating taxpayers into the tax system where their faith or other convictions led them to have objections similar to Day's.