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This Note draws on socio-psychological sources, conversations with experienced mediators, and dispute resolution literature to articulate a measured theory of when, where, and how apologies may play a role in dispute resolution. Avoiding both conclusory idealization and complete dismissal of apology, this Note argues that, in some disputes, apology is a powerful means of moving parties closer to settlement. Though apology is probably not the direct substitute for monetary compensation depicted by the casebook employment scenario, it may facilitate agreements on compensation by alleviating the psychic injury that makes parties unable to settle. Because apology may improve the dispute resolution experience for both parties, lawyers concerned about client satisfaction should consider attending more carefully to demands for apology. Indeed, lawyers skilled in crafting language may aid parties to exchange sincere regrets without making specific admissions of liability and thus pave the way for more fruitful dialogue.