A contract is a mutual exchange of legally enforceable promises. So in the event that one of the contracting parties breaches its promise, you would think that the non-breaching party could have the promise legally enforced. Well . . . not exactly. In the vast majority of contract disputes, instead of obtaining the legal enforcement of the promise, the non-breaching party is awarded damages. But in some situations, the most appropriate remedy is a court order actually requiring the breaching party to perform its promise under the contract. Still, many judges are reluctant to order specific performance because they do not want have to be involved in micromanaging whether the subsequent performance is made properly. Other types of contracts (such as personal services contracts) are not permitted to be specifically enforced. In those case, damages are the sole remedy.
Anecdotally, I once brought a lawsuit for specific performance against a commercial real estate developer. The trial judge found in my client’s favor, but adamantly opposed ordering specific performance, opting instead to award damages. After the Court entered its damages award, the parties settled the dispute for. . . you guessed it. . . specific performance.