The paper studies 7 new entrant smallholders on the Italian agricultural sector to begin to understand how such a grassroots movement may challenge the status-quo vis-à-vis the Italian Food-system. Additionally, the study conducts a public questionnaire survey in an attempt to gauge attitudes toward a changing food-system in Italy. Using Critical Theory to highlight the trend of critical-consumer to critical-producer, and transition movement theory to assess the real regime-change ability of such movements, this paper finds that new entrant smallholders in Italy are playing a potentially significant role in moving the sector into more sustainable territory. Current certified organic agriculture is increasingly dominated by larger farms, and excludes new entrant smallholders, this is to the detriment of sustainable agriculture goals, by identifying the barriers to such stakeholders, in addition to recognising their strengthens - namely the commitment to triple bottom line sustainability - new entrant smallholders have a significant role to play in making organic agriculture truly a mechanism by which true sustainable agriculture can be achieved.