When a contract is broken, American law does not set out to punish the breaching party; it sets out to make the injured party whole by protecting the position promised performance would have produced. This guide explains how courts actually build a damages award, starting from the compensation principle and the three protected interests--expectation, reliance, and restitution--and working through the foreseeability rule of Hadley v. Baxendale, the certainty requirement and the modern fate of the new-business rule, and the Uniform Commercial Code's precise buyer and seller formulas including cover, market differential, and the lost-volume seller's lost-profit measure. It covers liquidated-damages clauses and the penalty bar, the duty to mitigate, the near-total unavailability of punitive damages, the narrow band where specific performance is granted, and the often-decisive question of prejudgment interest and attorney's fees. A step-by-step worked computation shows the doctrines operating together, and a closing section explains why aggregate "award" statistics mislead more often than they inform. Clearly labeled hypotheticals illustrate every measure, and the guide ends with an FAQ and a plain-language disclaimer.