The daily experience of multistabilities of technical artefacts gives rise to the question of how we can make sense of them in the interaction. A historical and ontological review reveals that technology provides a more primordial way of knowing than science. A comparison between explanation and understanding in science demonstrates that a scientific explanation alone is insufficient for the acquisition of all knowledge. Achieving scientific understanding requires a confluence of a scientific explanation, human agency and social context. Having emerged as a key issue within the engineering-oriented philosophy of technology, the shared consensus of researches on technological explanation is that deductive reasoning is insufficient for producing a comprehensive explanation of function in terms of physical structure. Based on the pervious discussions, I introduce the notion “technological understanding” referring to sense-making in the interaction with technical artefacts in this paper. This understanding is unfixed and involves primitive, context-sensitive, re-interpretative and history-situated sense-making. A theory of technological understanding as a comprehensive exploration of human cognition should take all the conditions and factors of understanding into account. A preliminary analysis indicates that the affordances of a technical artefact, context and human agency are essential components for the technological understanding. In addition, the acknowledgement of and concern with sense-making of situated, context-sensitive meanings align with the core of hermeneutics. Therefore, taking hermeneutics of technology into account may provide productive insights for exploring technological understanding.