In the wake of ecological crises, there has been a resurgence of interest in the relation between dialectical thought and nature. The work of Herbert Marcuse and Murray Bookchin offers unique approaches to this question that remain highly relevant. In the first half of the article, we engage with Marcuse's application of the dialectical method in which he gestured to the “vital need” to push beyond the appearance of “the real” and yet lamented the loss of the ability for negative thinking to pierce the dominance of the “technical apparatus” that tied humanity to this “radical falsity”. Here, we suggest the need for a more holistic dialectical understanding of the social totality—one that is directly located within, and takes as foundational, the environmental conditions of human society. In the second half, we examine Murray Bookchin's conception of “dialectical naturalism” as a more thorough engagement with the human/nature relation that surpasses Marcuse's late engagements with ecologism. In particular, we offer critical reflections on the concept of “nature” in the contemporary ecology movement and illustrate how dialectical naturalism is capable of not only transcending dualistic conceptions of “man/nature” but in expanding our awareness of the potentialities of history along what Bookchin terms the “libertory pathways” to a restorative relation between human “second nature” and biological “first nature”. We posit that systemic, interconnected and accelerating ecological crises (climatic, biospheric and oceanic) form the objective and absolute contradiction of contemporary global social life that compels an awareness of the potentialities of an ecological society. Only through this awareness can we break through the reified “solutions” that have often plagued the ecology movement, bringing about the urgent social and ecological transformation that our species requires for its liberation and long-term survival.