Apprentices often have a hard time linking what is being done at school with what they experience at work in the host company. Everything differs between these two contexts – the setting, the colleagues and the possibility versus impossibility of reaching out to more experienced persons to receive help or ask questions whenever needed. Each location has its own agenda and programme. Nothing guarantees the matching of the content with the topic addressed since, with few exceptions, as in the very seasonal professions, each company may be working on a different topic at a given point in time. So, school information might come too early for some and too late for other apprentices of the same class. Can technology be of any help here? And how? The current chapter investigate if and under what conditions schools can provide help to apprentices in doing their work at the company and, hence, ease the job of VET trainers out there in the host companies. A story taken from the lessons given by a prominent teacher in the branch of painting illustrates this ‘boundary crossing’ scenario.