Headteachers of Catholic schools in England in the early twenty-first century are facing unprecedented challenges in exercising their role. In addition to concerns about funding and recruitment, leaders in Catholic schools are subject to challenges about Catholic identity and integrity, which are tested by pressures such as social media that have an impact not only upon the mental and emotional health of young people but on faith practice in families and in the community. Traditionally, the Catholic school community comprised a balance across the home, the parish and the school. However, pressures on home life and the reduction in the number of priests have often left the school as the single focus of the Catholic community. Catholic education, moreover, has been open to challenges from what Cardinal Cormac Murphy O’Connor called ‘aggressive secularism’, which questions the very existence of Catholic schools. In this paper, the writer explores contemporary challenges for headteachers in Catholic schools as expressed from the perspective of headteachers in one diocese in England. The research was conducted in two phases. In the first phase of the investigation, an open question was distributed at a diocesan conference of Catholic headteachers and deputy headteachers, inviting participants to indicate their three most pressing challenges. A phenomenological approach was adopted, and, through a process of Thematic Analysis (TA), five pre-eminent issues were identified.