AbstractVocational education and training (VET) at Swiss enterprises includes the work with various digital technologies. They ease administration of work hours, work tasks, evaluations or log book remarks; they support communication with peers, co-workers and trainers; and they come in handy for idea development and creative work. Overarching trends in terms of changing learning cultures in apprenticeship training, such as individualization, flexibilization, self-organized learning, project work or coaching, support the introduction of these technologies and also benefit from them. Based on three in-depth case studies, results on the usage and impact of digital technologies will be presented. This chapter addresses the following research questions: Which digital tools are used in workplace training? What are potential benefits and extended justifications for the use of digital tools? How are modern learning cultures impacting the use of digital tools? We will outline how and where digital technologies are used at the workplace in apprenticeship training, why management has introduced them and how apprentices and their trainers benefit from it. Based on our findings, we will draw conclusions about how learning cultures are influencing the use of technologies and vice versa how the introduction of these technologies shapes innovative learning cultures in VET.