The rail network relies on an extensive system of trackside drains to remove surface water and minimise the risk of flooding and damage to the network. Failure to maintain the drainage infrastructure can have significant cost and safety implications for the parent asset; such as delay minutes, poor track geometry, line closures and the likelihood of earthwork failures. Our focus is on improving the performance of the rail infrastructure's drainage system - a critical, yet often overlooked element of the network infrastructure in order to help "design, build and operate railway infrastructure at reduced cost". Our approach is to leverage previous work on an innovative self-learning system for maintaining drainage networks in the highways sector and adapt this technology – including the IoT sensor network, data models and decision support system - for use in the rail sector.