Companion friendship is a paradigm example of a trusting relationship and is a central good in human life. These friendships are also complex; navigating this complexity carries risk. Philosophical work has largely overlooked questions about how friends might navigate this morally risky space in ways that protect and develop their relationship over time. More specifically, although it is generally accepted that friendship involves acting to promote the well-being of one’s friend, ethical analysis of such interpersonal action has not addressed questions such as: How does acting for a friend’s well-being follow from and affect the trust within these relationships? What are the risks of acting for a friend’s well-being? Do genuine but unsuccessful attempts to promote a friend’s well-being, that bring about a rupture to the trust, necessarily cause lasting damage to trusting relationships? If not, why not? We argue that getting it wrong when acting for a friend’s well-being can provide an opportunity to protect and develop the trusting relationship, even while it causes harm to one’s friend and temporarily damages the relationship.