Most primary schools (for children aged 4–11 years) in England are maintained by the local authority, and only 39% of children attend academy schools. This is in contrast with the government’s recent ambition for all schools in England to join a Multi-Academy Trust (MAT) by 2030. This report considers the Department for Education’s (DFE) 2021 research findings that the reluctance of primary schools to join MATs is due to their concern regarding the loss of autonomy; this finding is compared with the spontaneous opinions obtained through the qualitative interviews of five retired primary school headteachers. The participants expressed that MATs treat headteachers poorly, and mentioned issues of competition and expandability. The DFE must attempt to alter this stereotype before the government executes its mass academisation plans. If this is not addressed, headteachers will join MATs fearfully, which will inhibit their ability to lead.