Historically, cities have been the repository and medium for our collective works, aspirations, and celebrations, driven by the promise of prosperity, wellbeing, and societal accord. Contemporary cities are technologically mediated in a manner that is reconfiguring the spatial and temporal conditions of the urban realm at an unprecedented scale and pace. We are experiencing a substantial transmutation of the material, utilitarian, everyday, spectacular, and symbolic reality of the urban, and with it, our capacity to be urbane, together. Although the design, construction, and operation of cities is seen as chiefly a practical and technical challenge, the “how” must be guided by questions of a fundamental, axiological nature – that is to say, questions concerning the values, ethics, qualities, political and aesthetic experience of urban life. Such qualitative values are most potently expressed in the artefacts and events of a meaningful and productive cultural life. Understanding the relationship between variously formal and informal modes of urban collectivity – referred to in this paper as citying – and the formal practices of city-making as a sophisticated cultural and technical enterprise motivates this inquiry. Furthermore, it will be argued here that such questions concerning culturally defined notions of values are inseparable from our ever-present awareness of humanity’s role in whole-scale environmental degradation otherwise known as the era of the Anthropocene. Thus, a triad is formed – culture–technology–environment – that fundamentally defines the way in which we make and inhabit contemporary cities.