This chapter focuses on the relationship between philosophy, pedagogy, and practice when designing programs/units/courses for transitioning students to new spaces in higher education. It offers both theoretical perspectives and case studies that reveal the successes and challenges of using philosophically driven pedagogies with diverse transitioning cohorts. The University of Newcastle published a report that detailed the ethos, values, and practices that constituted enabling pedagogies in their own enabling programs and proposed that enabling pedagogies are necessary across all areas of higher education. The term ‘transition’ in the context of higher education is used to describe the academic as well as social movement and acculturation of students into new educational spaces. Most poignantly educational philosophies provide “a holistic conception of people making and world-making”. Reflecting on educational philosophies allows one to examine which educational values are promoted and which are marginalised.