Apologies are an important part of moral life and a method by which someone can satisfy their reparative obligations. At the same time, apologies can be used both as a shield to protect the person apologizing and as a weapon against the person to whom the apology is owed. In this paper we unpack both claims. We defend two principles one should employ to try to avoid such bad outcomes: (1) Apologies must be one-sided and nontransactional, and (2) the wrongdoer must be willing to pay what they owe. We argue that these principles require the wrongdoer’s emotional vulnerability. Furthermore, we argue that the duty to be vulnerable in issuing apologies helps to make sense of why apologizing well is so difficult and why members of privileged groups might be especially prone to apologizing badly.