The use of mobile sensor methodologies in urban analytics to study ‘urban emotions’ is currently outpacing the science required to rigorously interpret the data generated. Interdisciplinary research on ‘urban stress’ could help inform urban wellbeing policies relating to healthier commuting and alleviation of work stress. The purpose of this paper is to address—through methodological experimentation—ethical, political and conceptual issues identified by critical social scientists with regards to emotion tracking, wearables and data analytics. We aim to encourage more dialogue between the critical approach and applied environmental health research. The definition of stress is not unambiguous or neutral and is mediated by the very technologies we use for research. We outline an integrative methodology in which we combine pilot field research using biosensing technologies, a novel method for identifying ‘moments of stress’ in a laboratory setting, psychometric surveys and narrative interviews on workplace and commuter stress in urban environments.