<p>Enactive perspectives on habit reject mechanistic models and call attention to the neglect of this concept in computational approaches to the mind. Recent work has brought enactive views on habit into dialogue with phenomenological and pragmatist perspectives, yet engagement with Hegel’s philosophy of habit has been scarce. We establish connections between Hegelian and enactive views on habit, showing their resonance in various registers, including the organic conception of habits and their transformative roles in sensorimotor and social agency. A closer engagement with Hegel echoes recent efforts to integrate dialectical thinking into the enactive framework. This includes elucidating the entangled relationship between biological regulation, sensorimotor agency, and social normativity, paving the way for the development of an enactive approach to social institutions. Looking at Hegel through an enactive lens, in turn, provides us with an operationalised, scientific interpretation of his organicist view of habit and challenges dichotomous distinctions between first and second nature. Even in this initial phase, this dialogue results in a naturalistic yet non-reductionist view of human minds, positioning habit as a key boundary concept for understanding the dialectical interplay between life, mind, and sociality.</p>