Defined as any activity where farmers are responsible for documenting and/or reporting on a particular indicator, self-monitoring confers a number of advantages, including the potential to increase the cultural acceptance and value of agri-environment work. Despite this enthusiasm towards the concept, there has been scant empirical research into its application and a failure to appropriately measure its contribution to the cultural acceptability of agri-environment behaviours. Given the widely documented failure of agri-environment schemes to engender a sustainable shift in farmer behaviour, an empirical assessment of self-monitoring is therefore both timely and significant. Drawing on 34 semi-structured interviews with farmers, land managers and allied professionals in England, this paper explores whether, by fulfilling the Basic Psychological Needs (BPN) of autonomy, competence and relatedness, self-monitoring could be an effective way to make agri-environment work and outcomes more appealing and sustainable within the farming community. The data affirms that self-monitoring has potential to fulfil the BPNs by (i) offering farmers a sense of ownership over their monitoring, (ii) equipping farmers with monitoring skills to enable them to recognise and value their effectiveness in producing environmental outcomes, and (iii) offering farmers a new way to feel and express connection to others in the farming community. I demonstrate how self-monitoring is capable of transitioning the way agri-environment work is perceived – from one of external regulation to one of an increasingly autonomous form of motivation (which is associated with greater performance and persistence). I also showcase the use of BPN in the agri-environment field. Having demonstrated the potential of self-monitoring to improve the cultural acceptability of agri-environment work, I appeal for further interdisciplinary research to follow-up with these initial findings; only then can the benefits of self-monitoring be fully realised in agri-environment policy design in the UK, Europe and beyond.