This chapter explores the profound and multifaceted challenge that postmodern and poststructuralist theories pose to the core tenets of modern philosophical thought, with particular attention to their complex and often ambivalent engagement with Hegelian dialectics. Through a rigorous analysis of seminal works by Jacques Derrida, Gilles Deleuze, and Michel Foucault, the chapter illuminates how these thinkers contest fundamental Hegelian categories—including contradiction, determinate negation—while advancing alternative philosophical frameworks grounded in difference, multiplicity, and discontinuity. At the same time, the chapter highlights the paradoxical relationship between postmodern thought and Hegelian dialectics: despite their repeated efforts to dismantle dialectical thinking, postmodern theorists frequently remain entangled in the very conceptual terrain they seek to deconstruct. The chapter critically examines the limitations of poststructuralism and postmodernism, particularly their efforts to repudiate dialectical thinking, by engaging with Fredric Jameson’s characterisation of postmodernism as “the cultural logic of late capitalism.”