In this thoughtful and provocative collection of essays, a group of scholars from varied backgrounds and interests have each taken up the educational challenges bequeathed by Dwayne Huebner in his 1996 essay, “Challenges Bequeathed”. Huebner encouraged educators to surpass the technical foundations of education, affirm the significance of the imagination, use the world’s intellectual traditions and achievements, engage in public discourse about education, and speak out for children and youth. Each author has extended, and in some ways transcended, the discussion of these five challenges yet still draw upon the considerable contribution Dwayne Huebner has made to the field of education. The writers in this volume grapple with the complexities of teaching and learning as always in process and as always relational; of schools as sites of creative and imaginative acts of knowing and being. The book begins with Huebner’s 1996 essay wherein he delineates the challenges for educators, as he perceived them. Readers are invited to begin with this chapter. However, after taking in Professor Huebner’s “prescience, his ability to see, years in advance of everyone else, what is deeply at work in present times, where it is headed, and what needs to be done about it...” (Smith, this volume) we encourage readers to dip into this volume randomly rather than in sequential order. While doing so, it is important to be mindful that “these challenges do not exist in isolation of each other; rather they are inextricably linked in myriad ways. Each one of these challenges requires consideration of classroom spaces, the individuals who occupy these spaces, and how these spaces are influenced by external forces” (Tupper, this volume). We invite you to take up a challenge.