New Zealand primary school teachers have shown interest in implementing learning through play programmes, and alongside this developing teaching pedagogy teachers are seeking an assessment method that appropriately aligns with the holistic nature of play. Learning Stories, commonly used in New Zealand Early Childhood Education settings (Mitchell, 2008), are formative assessment documents used to assess observed learning during play. Some primary school teachers with learning through play programmes have also started using Learning Stories to assess learning and progress of students. Using a Sociocultural lens, this qualitative research explored how teachers from three New Zealand primary schools are using Learning Stories assessment. Undertaken as an appreciative inquiry, this research, grounded in an interpretivist paradigm, used a multiple case study approach, collecting evidence through semi-structured interviews and gathering relevant documentation to investigate how the participant teachers from three case study primary schools were using Learning Stories. The research provides an insight into the participants’ views about the use of Learning Stories in their primary school settings. There is little existing research about the use of Learning Stories in primary schools and this research provides interested educators with some of the benefits for using Learning Stories in a primary school context. Key findings within this research indicate that Learning Stories are an effective way to assess both dispositional and academic progress, for highlighting learner strengths, and providing a framework to assess progress over time.