Calf morbidity and mortality rates are often high in dairy herds, raising animal welfare concerns and negatively affecting farm economic efficiency and future performance. Disease prevention is critical to maintain calves in good health, but interventions are dependent upon the persons conducting them. This paper explores the perceptions of farmers, farm workers, veterinarians, and other advisors on the management of calfhood disease on dairy farms in England. Participants were recruited using purposive and “snowball” sampling, resulting in 40 in-depth, semi-structured interviews—26 with dairy farmers and 14 with advisors. Interviews were recorded, transcribed, and thematically coded. Three major themes were derived on the basis of interview data: disease occurrence and treatments, management of calf environment, and the role of stockmanship and perceived control. Respiratory and gastrointestinal diseases in calves were those reported to be most problematic on dairy farms. Limited time and financial resources caused some farmers and advisors to experience a perceived inability to control calf health without antimicrobial treatments. Overall, the findings emphasise the importance of human influences on calf health and disease in the context of influencing the interactions among the host, pathogens, and the environment. Further research should investigate what “attention to detail” means within different farm contexts and practices, as this was believed to be important in the promotion of better husbandry standards and health. We recommend the use of supportive knowledge exchange processes, including facilitation, to empower farmers to promote continuous improvement in calf health.