In situated and embodied approaches it is commonly assumed that the dynamics of sensorimotor engagement between an adaptive agent and its environment are crucial in understanding natural cognition. This perspective permits to address the symbol grounding problem, since the aboutness of any mental state arising during agent-environment engagement is guaranteed by their continuous coupling. However, cognitive agents are also able to formulate representations that are detached from the current state of affairs, such as expectations and goals. Moreover, they can act on their representations before—or instead of—acting directly on the environment, for example building the plan of a bridge and not directly the bridge. On the basis of representations, actions such as planning, remembering or imagining are possible that are disengaged from the current sensorimotor cycle, and often functional to future-oriented conducts. A new problem thus has to be acknowledged, the symbol detachment problem: how and why do situated agents develop representations that are detached from their current sensorimotor interaction, but nevertheless preserve grounding and aboutness? How do cognitive agents progressively acquire a range of capabilities permitting them to deal not only with the current situation but also with alternative, in particular future states of affairs? How do they develop the capability of acting on their representations instead of acting directly on the world? In a theoretical and developmental perspective, we propose that anticipation plays a crucial role in the detachment process: anticipatory representations, originally detached from the sensorimotor cycle for the sake of action control, are successively exapted for bootstrapping increasingly complex cognitive capabilities.