This article examines one of the most important ethical tensions that arise in legal writing—zealous advocacy versus candor to the tribunal— and explores how to educate, sensitize, and train young lawyers so that they may effectively navigate the boundaries of this conflict. Although this tension is manifested in a myriad of choices legal writers make, ethical issues arising in the context of written documents are generally not discussed in law school. Consequently, a law student may graduate with no appreciation for the complexities of ethical issues that arise in legal writing and without the tools to address those issues. To understand the dilemma confronting novice lawyers, this article analyzes the tension between the duties of zealous advocacy and candor; explores the judiciary’s inconsistent response to attorneys’ fulfillment of these duties and its impatience with a perceived lack of candor; examines the education presently provided to law students; and suggests various pedagogical and practice-based techniques that will heighten the novice legal writer’s awareness of and ability to embrace these dual ethical duties. This article concludes that legal education, specifically legal research and writing courses, must alert students to the ethical issues manifested in legal advocacy documents and provide students with the tools to draft ethical and effective legal arguments.