Among the transitions during a pupil's school career, the transfer from primary to secondary school arguably has the most impact. Far from being linear, this transition is a kind of "pupil pilgrim's progress"; a journey with orientations, stops and reorientations, checking and refining skills that the pupils bring with them from primary to secondary school. The research presented here focused on this period of transition and aimed to explore to what extent pupils who had experienced a well-embedded Assessment for Learning (AfL) approach in their final year of primary school (Year 6 in England) would be able to build on and use their acquired learning skills in the first year of secondary school (Year 7). The pupils were interviewed at critical stages during the transition. They appeared confident in their skills at the end of Year 6, rather disoriented in the first term of Year 7, slowly regaining confidence in their learning skills after adapting to new routines in the following term. Only at the beginning of Year 8, the second year at secondary school, did pupils fully regain their confidence, enabling them to deepen their understanding of their learning, and to progress. Three key elements--consistency, confidence and challenge--when present in a balanced way, can facilitate the process of transition. It became clear from the pupil narratives that a cross-phase conversation between teachers needs to include how to build on pupils' learning skills and engage pupils as active agents in the process of progressing their own learning. The pupils' experiences of AfL appear to have provided a sound basis for this agency. Whilst the research has implications for all subjects at transition, this article applies these findings to the context of modern foreign language learning. (Contains 1 note.)