We synthesize the interdisciplinary literature into a heuristic for crafting effective organizational and supervisory apologies (the OOPS four-component apology). In the first experiment, we demonstrate how an offense committed by an organization is perceived to be more egregious than an offense committed by a friend or supervisor. Furthermore, results did not support that OOPS apologies are unequally effective if issued by a friend, supervisor, or organization. In the second experiment, we test OOPS apology-training effectiveness. Results indicated that trained participants crafted more effective apologies. Our apology heuristic is an innovation for training business communicators how to apologize effectively.