Agricultural employment in advanced economies has been suggestively described as a “short and step” pyramid with only limited opportunities for workers to climb to higher positions, especially when they belong to the most vulnerable categories, such as migrants. The presence of poor jobs and living conditions for temporary agricultural workers reported by mass media, trade unions, NGOs, and international observers contrasts dramatically with the idea of a modern and thriving sector, as the Italian agricultural sector should be, and it represents a challenge for the social concerns that have been alongside environmental ones in the definition of sustainability since the Brundtland Report released in 1987 by the World Commission on Environment and Development (WCED). Even mechanisation does not necessarily facilitate better working conditions. In fact, where the workforce is largely replaced by machineries, the remaining opportunities for paid workers are mainly for unskilled, physically demanding, and seasonal jobs. This has brought about the so-called “paradox of prosperity”, where the gap between farm and nonfarm workers in economically advanced countries has widened in terms of wages, benefits, and prospects for upward mobility. This in turn triggers a vicious circle with a structural lack of available workforce for the sector, which has been increasingly provided by migrants with very little bargaining power. On the other hand, the adoption of new technologies and digitalisation in agriculture is leading to an increasing demand for skilled workers, which often remains uncovered because of the low conditions offered. Against this background, the aim of our work is twofold. First, we characterise the role of the foreign workforce in relation to the structural changes in Italian agriculture and considering territorial differences. Second, we examine the main policy instruments to facilitate recruitment and tackle undeclared work and more specifically the Quality Agricultural Work Network (Rete del lavoro agricolo di qualità) launched in Italy in 2016 to tackle undeclared work and exploitative labour. We do so by conducting a literature review and semi-structured qualitative interviews with 16 farmers in Italy carried out in 2022 within the project Rural Social ACT funded by the Asylum, Migration, and Integration Fund (2021–2027). The results show that even though foreign workers are a key resource for agriculture in Italy, there remain severe recruitment issues and segregation in low-skilled and precarious jobs. Overall, it is necessary to improve the awareness of the key role of work in agriculture and to strengthen the effectiveness of tools to enhance the visibility of compliant farms. So far (January 2024), only 6600 farms have joined the Quality Agricultural Work Network, with an overall modest enthusiasm from the farmers interviewed about its current effectiveness. Other instruments are explored such as employee sharing contracts, and there clearly emerges a need for public support of professional training through the Common Agricultural Policy to improve both the bargaining power of foreign workers and the productivity of the sector.