An IT tool has been designed aimed to support the management of an enterprise exposed to the conditions of risk and uncertainty. The main component of this tool is a generator of random train timetables in a railway undertaking. The generator produces input data that can be used to forecast a departures timetable in rail transport. The tool can generate both random timetables as well as allowing real quantitative data to be entered manually. The idea of the solution is based on the MS Excel spreadsheet whose built-in functions were used to model random rolling stock timetables in a railway company.