In many organizations, subsidiary performance goals are developed remotely by optimistic leaders back at headquarters, leaving deployed managers vulnerable to unrealistic operational expectations on the frontline, unable to follow orders. Most management research categorizes employees’ failure to follow workplace directives as deviant behavior. In contrast, I argue that in some circumstances ‘disobeying orders’ should be considered a virtuous, responsible leadership strategy when facing unachievable tasks. Through a historical analysis of the surrender of the British colony Singapore to Japan during World War II, this paper links pro-social rule breaking (PSRB), productive resistance, and responsible leadership literatures, developing a process model that explains how some deployed leaders cope with ethical dilemmas in virtuous ways by ‘disobeying orders’.