In this hyperconnected, dynamic world we live in, permeated by profound challenges and transformations, the awareness of complexity is unequivocally on the rise. This monograph argues that it is high time that our educational institutions and pedagogical approaches come to mirror this growing awareness, to assist and inspire humanity to embrace complexity, to learn to move within it with increasing sensitivity and wisdom. Doing so is necessary, for if there is one thing that the years behind us bear witness of, it is that the tendency and attempt to simplify, separate, control, and indeed exploit has – as the dark side of the advancements of modern life – brought upon us unprecedented ecological and humanitarian crises. Schools, notably, are not closed spaces separated from society but open places within society, and as such they are inevitably complicit in the (re)shaping of our shared world. This book, therefore, proposes an ambitious pedagogical agenda. Specifically, it explores the relational ontological premise of entanglement in the context of pedagogical theory, raising the question of how, as teachers, we might meaningfully and responsibly engage with the myriad ways in which students are simultaneously shaped-by and shapers-of contemporary societal challenges. In close collaboration with twelve teachers as co-researchers, the book offers six ''helpful perspectives'' for teachers seeking to embrace such complexity in their own practices, referred to as: (1) entanglement-orientedness, (2) entanglement-awareness, (3) hopeful action, (4) inquiry within entangled phenomena, (5) practicing perceptiveness, and (6) practicing integrity.