Farmers from all commodity groups encounter different stressors; livestock farmers especially grapple with choices that muddle ethical, emotional, and economical boundaries. Canadian farmers experience higher levels of anxiety, depression, perceived stress, and are at an elevated risk of burnout in comparison to the general population, and animal-care related occupations also experience higher levels of psychological distress. Agriculture is rooted in culture and tradition, and being a ‘good farmer’ is frequently part of one’s identity (Burton, 2004). In animal agriculture, on-farm technology is promoted to enhance farmer well-being, animal welfare, and/or environmental sustainability. As such, technology has advantages but the fundamental changes it brings to the farmer-cow dynamic cannot be ignored. The objective of this study was to explore dairy farmer well-being in the context of (1) animal health and welfare, and (2) on-farm technology. I conducted semi-structured interviews to address these objectives and conducted a thematic analysis for each. I found that the emotional and physical act of caring for livestock, as well as the connection to their animals, may play a role in dairy farmer well-being, serving as both a risk and reward. It was evident that technology can be of benefit when used as a tool, if appropriate for the farmer and the specific on-farm context. In both research chapters of the thesis, external pressures were an added source of stress for farmers which underscores that many stressors are out of their control, particularly when it comes to feed sovereignty and weather, uncertainty, economic volatility and labour shortages, and structural inequity.