The objectives of this study were to identify caretakers’ perceptions and stressors related to performing on-farm euthanasia as well as potential ideas for intervention strategies to alleviate negative effects of performing euthanasia on caretaker well-being. Additionally, we aimed to determine how euthanasia methods, procedures, and training correlate with dairy caretakers’ attitudes toward performing on-farm euthanasia and their job satisfaction and sense of well-being. Thirty-eight dairy caretakers (19 workers, 15 supervisors, 3 owners, 1 veterinarian) participated in focus groups or interviews conducted and recorded on five Northern Colorado dairies. Thematic analysis of focus group and interview transcripts revealed seven recurring themes. Variation in available training and euthanasia protocols among dairy farms was evident. There was a lack of awareness regarding available mental health resources and little communication between farm personnel about euthanasia-related stress. Training was correlated with caretaker knowledge about euthanasia procedures and the language used to refer to euthanasia. Human-animal bonds and empathy toward animals were evident in participants regardless of training, job position, or dairy experience. Interventions such as training programs, mental health resources, and other support systems should be tested for effectiveness in addressing euthanasia-related stressors, improving euthanasia decision-making and practice, and increasing animal wellbeing on dairy farms.