The European railway network includes more than 300 000 km of tracks, widely connecting all cities and towns and representing a key asset in the European transportation ecosystem. Maintenance is essential to ensure safety and sustainability. In this context, the EU-funded Shift2Rail project DAYDREAMS will set a course for the integration and use of data and artificial/human trustworthy intelligence together with a context-driven human machine interface (HMI). Specifically, it will improve the decision-making process and design advanced context-driven HMIs to allow context- and risk-aware multiple-options decision-making processes. The project will validate its proposed solution using several scenarios. The validation will test the solution and its suitability for future adoption in multi-actor environments.