The standard attribution of ought implies can rules out the possibility of Kantianism permitting the existence of moral dilemmas. Against this, I argue that Kantianism both can and should permit the existence of moral dilemmas. This new take on moral dilemmas should be of particular urgency to those hoping to radicalize Kant, I argue, because the work of oppression theorists shows that moral dilemmas are particularly likely to strike those who are already most vulnerable. The insights of oppression theory also suggest that the heretofore overlooked social and political implications of moral dilemmas are just as philosophically significant as the metaethical and ethical implications.