The international governing body for equestrian sports, the Fédération Equestre Internationale (FEI), states that the welfare of the horse must be paramount and never subordinated to competitive or commercial influences. However, there is growing unease about welfare issues from both within and outside the sport. The aim of this study was to understand stakeholder perceptions of current welfare issues within equestrian sport, determine whether there is scope for change, and explore attitudes towards welfare assessment. Participants (n = 48) from equestrian sport (n = 38) and animal welfare research (n = 10) attended a workshop that included welfare-related presentations and focus group sessions. The focus group sessions were recorded, anonymised and analysed using thematic analysis. Conflict between the demands of competition and the needs of the horse was identified as a key welfare challenge. Although the physical health of equine athletes is closely monitored, horses’ psychological needs are sometimes overlooked. Participants recognised that improving competition practices may not be as impactful as improving the general management and training of horses. The term “quality of life” was considered preferable to “welfare”, which had negative connotations. Participants appreciated the idea of incorporating formal welfare assessments into their training and competition plans but stated that existing tools are rarely used and are not deemed feasible for real-life conditions.