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The criminal sanction is generally considered a means of last resort in the regulation of securities fraud. It is most widely used in instances where no other remedy appears feasible, or as a deterrent in areas where criminal behavior appears to be trending. As one weapon in the arsenal of enforcement remedies, there is little evidence to indicate a principled approach in guiding answers to the central questions of why punish and how much? This paper traces the use of the criminal sanction in cases of securities fraud and examines the role of punishment in relation to more widely used compliance-oriented enforcement approaches.