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In Japan, the vast majority of transport companies are small or medium-sized enterprises (SME), and do not have any personnel specialising in health management. This report aims to elucidate driving operations managers (DOMs)’ efforts as well as difficulties faced therein in order to grasp the current state of and issues in the health management of truck drivers.We asked DOMs of six SME and three large transport enterprises (LE) questions, related to considerations given to the health of drivers, in semi-structured interviews for each. We first identified efforts being made and difficulties faced in these two groups. Then, we used a content analysis method and analysed them.Regarding efforts being made for the health of drivers, DOMs at SEMs spoke a considerable amount about handling drivers on an individual basis: understanding their usual conditions and discovering their changes through meetings and conversations, as well as checking and listening in a way that takes into account drivers’ individual characteristics and backgrounds. DOMs at LE considerably discussed systematic efforts. These included preventions to not increase drivers’ burdens and loads, utilising health management professionals. With regard to difficulties, DOMs at SME mentioned the difficulty of interpreting health examination results as well as that in addressing health issues due to vague judgment criteria.Differences in the approaches of LE and SME became clear. At LE, health management was being carried out systematically in coordination with health management professionals as part of driving operations management. On the other hand, at SME, drivers’ health was attended to on a more case-by-case basis by. It appears that there is a need for DOMs at SME to have more enthusiasm and competence when it comes to health management, as well as to receive more supports in, for example, interpreting health information.