The changing nature of war and expanded use of asymmetrical warfare practices has been well documented within both mainstream International Relations scholarship and critical approaches to the field, including feminist theorizing. What have been less examined to date are the complex and contested moral questions raised by these transformations in war, corresponding with analyses of how such shifts impact the ethical lenses through which combatants and civilians view political violence. In reflecting on the ethics of counterinsurgency, this paper brings these questions to the fore and asks how a feminist ethics of care approach can contribute to the development of a new understanding of what it means to ‘win hearts and minds’. I argue that the hypermasculine ‘warrior ethos’ which has come to dominate the behavioural character of most modern militaries is incompatible with the relational nature of counterinsurgency operations, producing an acute need for increased attention towards empathy and cooperation. The paper seeks to highlight the significant moral and ethical tensions present in post-9/11 counterinsurgency operations, and to demonstrate how a feminist ethical framework foregrounding care and empathy allows us to look more attentively at the particular contexts, lived experiences, and encounters impacting judgments about the morality of contemporary war.