Purpose: This paper aims to examine how instructional videos produced by retail employers and tech companies have modelled cashier roles and skills in service encounters over time, providing insights into cashier training and job responsibility evolution across different retail eras. Design/methodology/approach: Online video research is used, with YouTube as data source and the theory of practice architectures and related concepts as analytical framework, to examine 50 instructional video narratives produced between 1917 and 2021. Findings: Cashiers' selling practice comprises transactions and customer service, which are often taught separately. Technology has explicitly influenced changes in cashier work and training at three points in history: mechanised checkout (1917), computerised checkout (1980) and connected checkout (2010). "New technology" involves a combination of arrangements with the potential to transform the semantic, physical and social dimensions of cashiers' selling practice. However, despite technological advancements, employers' cashier training videos have not evolved significantly since the 1990s and still focus on emotional labour skills. Practical implications: The findings indicate a need for transforming training for service work in the connected service encounter. Originality/value: The relationship between technological innovations and changes in frontline service work and workplace learning is examined through the lens of instructional videos produced by retail employers and tech companies, giving rise to insights into limitations of current training methods for service workers. This paper suggests the need for a more holistic perspective on service encounters to understand service work and workplace learning changes.