With the aim of disclosing the antecedents and dynamics of food loss generation in the upstream stages of the fruit and vegetable sector, this paper presents the results of a series of semi-structured interviews with 10 Producers’ Organisations (POs) in Germany and Italy. The content of the interviews is analysed by applying a qualitative content analysis approach, thus disclosing the most relevant issues affecting food loss generation at the interface between POs and buyers (industry and retailers). Several similarities emerge as we compare the answers provided by Italian and German POs, especially concerning the role of retailers’ cosmetic specification on products in the generation of losses. Instead, the structure of contracts regulating commercial transactions between POs, industry, and retailers show noticeable differences, apparently resulting in a greater capacity to plan the demand of products from the beginning of the season in the Italian context. Despite these differences, this study confirms the key role of POs in increasing farmers’ bargaining power against the buyers, both in Germany and Italy. Further research is needed to compare circumstances in other European countries and to analyse why the similarities and differences identified occur.