Learning design is growing in importance but is not yet widely adopted by teachers. This paper describes the development of a scenario-led learning design process, divided into two stages, which was implemented with over 500 teachers altogether from 15 European countries. Activity theory is used to explore the contradictions that arose when such changes were introduced into the established activity system of lesson planning. Data were collected through interviews and questionnaires from a small sample of participants including national coordinators (stage 1: n = 8; stage 2: n = 13) and teachers (stage 1: n = 13; stage 2: n = 23). These participants perceived that the scenario-led learning design process, involving a wide range of stakeholders, was collaborative, supportive and innovative (compared to previous lesson planning practices). However, a number of contradictions were identifiable between: (1) the shift to collaborative learning design from teachers preparing their lessons alone; (2) the new tools and the existing rules of the national/regional education systems; (3) the time required to both understand and implement learning design, and the impact of competing demands. This paper discusses the challenges faced when attempting to scale-up European school teachers' development of digital pedagogy. The structured (yet flexible) approach was welcomed and the tools promoted teacher reflection but, as commonly noted, the complexity and time-constraints were major issues.