William B. Barker defines tax avoidance in terms of following the letter of the law while circumventing legislative intent. The chapter, a reprint of a 2009 journal article, considers tax avoidance that ultimately is detected and successfully challenged in court. The author takes issue with moral neutrality exhibited by the judiciary in the United States toward this type of tax avoidance, arguing that tax planning techniques that intentionally create and exploit ambiguities in tax statutes should not enjoy the degree of tolerance currently allowed.