This chapter will examine the assessment of damages for fraudulent misrepresentation in England and Wales. In so doing it will explore the nature of the damages awarded in such cases, highlighting the punitive and deterrent objectives inherent in such awards. The aim of the chapter is not to argue whether or not private law is the correct forum for punishing individuals. Rather the aim is to argue that, at times, judicial attitudes toward damages for fraudulent misrepresentation are “over-zealous”; and that, if punishment is appropriate in this arena, a much more measured approach needs to be adopted. The chapter will argue that the current law can grossly over-compensate the claimant whilst punishing the defendant in a disproportionate manner. The chapter will also make suggestions for the reform of this area of law.