Recently, the need for a more holistic approach to welfare assessment has been highlighted. This is particularly pertinent in the case of working equids who provide vital support for human livelihoods, often in low- to middle-income countries, yet suffer from globally low standards of welfare. This study aimed to provide insight into the welfare status and traditional use of working equids in rural Western European communities using the new EARS welfare tool, designed to provide a broad view of the welfare of working equids and the context in which they are found. Other questions on the topics of equid management practices, social transmission of expertise, environmental stressors, and traditions, alongside physical and behavioural welfare assessments were also included to explore the impact of these wide-ranging factors on an understudied population of working equids. The protocol was trialled on 60 working equid owners from communities in Portugal and Spain where, despite the decline in traditional agricultural practices and livestock keeping, donkeys and mules remain working animals. Many owners stated that the help donkeys provided was invaluable, and donkeys were considered to be important for both farming and daily life. However, participants also recognised that the traditional agricultural way of life was dying out, providing insights into the traditional practices, community structure, and beliefs of equid owners. Questions investigating the social networks and social transfer of information within the villages were effective in finding local sources of equid knowledge. Overall, welfare was deemed fair, and the protocol enabled the identification of the most prevalent welfare problems within the communities studied, in this case obesity and the use of harmful practices. The findings suggest that the new protocol was feasible and detail how contextual factors may influence equid welfare. Increasing understanding of the cultural context, social structure, and attitudes within a community, alongside more traditional investigations of working practices and animal management, may, in the future, help to make equid welfare initiatives more effective.