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Jury instructions on damage awards are notoriously vague and ambiguous. As a result, awards are sometimes unexpected and seemingly illogical. In this article, the authors argue that jury instructions regarding damages are vague because the law of damages itself is purposefully ambiguous—allowing particularized justice across a variety of different circumstances. The authors review research on comprehension and application of substantive jury instructions related to damages and on procedural variations at trial (e.g., use of preinstruction, bifurcation, blindfolding jurors to various issues, special verdict forms, caps on damages, and instruction revision) that impact the substantive instructions that jurors receive from the judge. They comment on attempts at reforming jury instructions regarding damages and conclude that jurors’ decision making on this difficult and emotional issue could be made more predictable by careful reforms at the trial level.