Food and nutrition security in high income countries is challenged by financial crisis, austerity policies, unemployment and immigration and a growing number of people, also from those segments of population once considered secure, seek food assistance. Emergency food initiatives are developed by a diverse range of actors through various instruments and approaches. Alongside the difficulties of this sector – lack of control over donation, inability to ensure nutritional requirements, stigmatization, dependency on volunteer work – new challenges emerge from welfare expenditure cuts, the reorganization of EU funds for the most deprived (FEAD) and from the spreading of surplus food recovery practices. Based on a preliminary analysis on food assistance practices in Tuscany (Italy), it emerged that operators involved in food assistance activities are re-thinking their role to address changing needs: private companies are increasingly involved in food assistance operations and adjust their activities and strategies accordingly; public institutions re-think the boundaries between charitable assistance, welfare system and market-based food system. How is food assistance re-thinking its role to deal with the challenges posed by the current context of change? This work combines the strengths of two approaches by developing back-casted pathways and testing them within explorative scenarios, that describe plausible future contexts. The aim is to explore the feasibility of transformative change in different scenarios. We apply a participatory scenario approach, as a tool for future-oriented thinking, mindful of future uncertainty and the multidimensional scope required to look at planning context. Results comprise the definition of shared priority themes: governance, education and a person’s centered approach. For each, key objectives were identified and back-casted plans of actions were developed, considering a suitable time frame. These plans were then tested within and across four different scenarios of the food assistance system. The methodology provides a promising learning tool to engage with stakeholders and foster a creative future oriented thinking approach to food assistance system’s vulnerability and resilience.