What does it mean to understand technology? While understanding has been extensively analysed in philosophy of science, it remains comparatively underexplored in relation to technology. Drawing on the concept of scientific understanding (De Regt, 2017), in De Jong and De Haro (2026a,b) we conceive technological understanding as the cognitive skill involved in engaging—practically or conceptually—with technologies. More specifically, it is the ability to realise an aim by using a technological artefact. The notion of technological understanding thus foregrounds the epistemic dimension of engaging with technologies: every successful use of a technology involves some form of understanding. Yet what counts as ‘use’, and which specific cognitive skill it requires, depends crucially on context. This presentation develops this insight into a systematic, contextual account of technological understanding. I argue that technological understanding is a family of context-relative cognitive skills that admit of degrees. To capture this, I distinguish three typical contexts of technological engagement: design, where artefacts are constructed; operation, where they are practically used; and innovation, where new applications are devised. In each context, technological understanding takes the form of a specific cognitive skill: the ability to design an artefact, to operate it, or to envisage and evaluate its possible uses. Correspondingly, artefacts must be intelligible in different ways: in terms of their inner workings (design), their practical performance (operation), and their functional possibilities and limitations (innovation). In the second part of the talk, I discuss how technological understanding (TU) fruitfully interacts with technology assessment (TA). Drawing on TU, I reconstruct Grunwald’s hermeneutic circle for TA as a combination of inter‑level feedback and intra‑level collective deliberation. I argue that this explains the co‑evolution of technology and societal meaning, and that it puts TA’s hermeneutic talk on a more rigorous analytic footing. Taken together, these results illustrate how TU and TA mutually illuminate and complement each other.