Including Denmark, modern pig production typically involves annual culling rates close to 50%. One important professional group in this process are livestock drivers transporting the animals to slaughter. By use of oral interviews, we aimed to describe experiences and opinions of Danish livestock drivers transporting sows, regarding fitness for transport and management choices relevant for animal welfare. All livestock drivers (N = 30) associated with a large slaughterhouse in Denmark accepting sows were approached in person, after having unloaded sows, and asked questions by an interviewer. A total of 22 livestock drivers (73%) answered all questions, constituting of a heterogeneous group of men of varying age, level of experience, time since they achieved the legally required certificate of competence, and daily involvement in sow transportation. Among livestock drivers included in the present study, doubt about fitness for transport was not uncommon, and specific reasons underlying their doubt were listed. All respondents reported to have experienced having to reject loading a cull sow who had been selected for slaughter by a herd manager, and approximately 40% did this several times a year. In contrast, almost 50% had never experienced having a sow rejected by the veterinarian at the slaughterhouse due to lack of fitness for transport. When asked about their management of sows during transportation, the majority (71%) reported using special condition transport (use of extra bedding and partitions to separate individual sows from rest of the load) less than once per month. All respondents considered hot days a problem for welfare of sows and the majority reported to adjust air intake of trucks daily or several times per week. In addition, approximately half of the respondents mentioned stationary periods (e.g., mandatory driver rests) as a challenge to sow welfare, to a degree where they had violated regulation on mandatory driver rests for the sake of welfare of the sows. The present study is among the few to focus on livestock drivers transporting sows, including questions about management choices and the animals’ fitness for transport. The findings may form basis for future development of educational programs for drivers as well as for the formulation of hypotheses for future studies in this area, characterized by complicated underlying legislation and challenges to animal welfare.