The built environment (BE) is currently undergoing a digital transformation from traditional to digital, affecting among others, architecture. Departing from the implicit assumption of digital technologies (DTs) for economic growth, productivity and performance, we instead focus on employees’ experiences of digital transformation and their well-being. DTs such as building information modelling (BIM) are used by architects at the front end of the project life cycle. As opposed to most past studies on well-being of blue-collar workers, we focus on white-collar workers. Architecture has a traditionally low job satisfaction and high prevalence of stressors that negatively impact well-being, and DTs could potentially affect job satisfaction in terms of creativity, autonomy, time pressure, menial tasks, career prospects, organisational commitment and potential. This chapter builds upon literature review and pilot interviews with healthcare architects/designers who were at the front line of the COVID-19 pandemic with NHS architects, creating new wards and vaccination centres, while private healthcare architects designed new hospitals. Although healthcare architects were in their busiest year, the DTs available to them could only support limited tasks and did not link well to asset operation. We explore how DTs transform the well-being of architects. Understanding well-being in architecture in light of digital transformation is crucial for creating the necessary leadership for the sector to grow.