The policy context for schools in England places great emphasis on leadership and autonomy as drivers of educational improvement. The purpose of this article is to explore how we can better understand, in this context, the challenges of leadership and autonomy and the conditions of leadership development that support or hinder the practice of ethical autonomy. The article summarises analyses of autonomy and the conditions affecting leadership preparation and development in England; in presenting the first of these two analyses, a definition is established of autonomy as adopting for oneself the principles to guide ethical action. The outcomes of the analyses are then considered together in order to frame thinking about the challenges entailed in autonomy and leadership. A key proposition is that principled autonomy is at the heart of this frame of thinking. At the conclusion of the article, implications are suggested for school leaders concerning the conditions for leadership development in schools.