Fleet management systems have been widely used in the maritime industry. Traditional fleet management systems focus on the whole vessel/ship. With the emergence of the Internet of Things and new smart technologies, smart fleet management systems are now embedded with greater power in comparison with traditional solutions, e.g. can be used to monitor the performance, status and behaviour of not just the whole ship but crucial internal components, such as engines, water treatment equipment, and propellers. However, developing, implementing and operating such new generation of fleet management system may not be straightforward and can encounter a wide range of socio-technical challenges, which have not been adequately explored in the current literature. This paper attempts to fill this knowledge gap by critically discussing these challenges, with practical suggestions drawn.