The idea of transmedial organisation emerged as the form adopted by much of today's storytelling, combining different media, at different points in time, placing the user in a new situation with a much more active attitude, having to work out how to understand a set of message and having to engage in the understanding of the story (Jenkins, 2006). Transmediality has some educational consequences that set it apart from other approaches, even outside specific learning contexts. Some of the ideas discussed led to the creation of a project entitled The Ancestral Letter, a transmedia story, designed and produced specifically for 15-year-old students. The project was implemented in two secondary schools in Barcelona in order to verify the interest in this concept. The journey we have made, from a few starting principles and theoretical problems to a complex case of transmedia storytelling, clearly highlights the difficulty involved in addressing the question of learning between contexts, and through them, especially if it is carried out in a simple and simplified manner; that is, without having a much more elaborate theory of learning contexts, nor a rigorously designed descriptive language. The Ancestral Letterand other transmedia examples offer us a more understandable and effective way of coordinating between the school-based and informal settings, between the digital setting and everyday life (analogical, not mediated by screens), both in terms of the organisation of content and in respect of time-based narrative. Unfortunately, we still do not have enough knowledge about this or about activity contexts (whether or not learning takes place within them).