Protected cropping is recognised as a highly productive but intensive farming system, with a covered area steadily growing worldwide, and research has been mainly looking at solutions to improve the sustainability of these productions, particularly in terms of long-term soil fertility and agrobiodiversity enhancement, which become even more relevant if production is certified organic. However, no extensive research has been dedicated to the more social aspects of this agricultural sector, therefore this study aims, through the employment of a mixed methods approach comprising online surveys and semi-structured interviews, at gaining a better understanding of how organic growers identify practices that affect their management the most, those factors of any given nature that have major influence on their decisions about improving and/or implementing these practices, and any potential benefits to it. The study also acts as a comparative analysis between two case-study countries, Italy and the United Kingdom, which will help shed light on differences and commonalities between the groups of producers, and give a better understanding of the strengths and weaknesses of each country. Survey results showed that growers from both countries rated fertility management the highest in terms of importance for their management; biodiversity conservation and landscape protection were rated higher by Italian growers, while energy efficiency and weed management were considered more important by British producers. Issues like short food supply chains, product traceability and traditional knowledge were considered equally relevant by both groups of respondents, since most were small-scale and rooted into local economies. Face-to-face interviews revealed differences between producers within and between scales of operations, showing that the level of intensiveness they employ inside greenhouses is more varied than what literature shows, and it links up to multiple factors (e.g. crops, growing season, available technologies, scale, channels of distribution), which also have a potential influence on growers’ management practices, which vary accordingly to how intensive the cropping system is. For organic growers, employing protected structures is commonly considered a necessary step for production, regardless of business size, to shelter crops from extreme events and to place produce on the market during the yearly ‘hungry’ gaps, and it is a trend that is likely going to continue in the future too, with greater protected areas, higher quality production, and a more effective resources management; therefore, a policy integration of a ‘greenhouse clause’, in terms of coverable areas and applicable practices, would be a step forward in setting pertinent rules for protected cropping systems. Given the different environmental conditions from the open field, maintaining a healthy and fertile soil in protected cropping is a shared priority among organic growers along with diversification of crops, products and market channels, to reduce vulnerability and better adapt to unexpected changes. Pursuing an increasingly sustainable and resilient system would also require a wider availability of training and education for growers, the facilitation of information exchange between them and other stakeholders such as scholars and policy makers, the possibility to share values, hard work and earnings in the form of cooperatives, and the importance of protecting small holdings, whose practices are usually deeply embedded in local contexts and whose survival depends on short supply chains and community support.