Urban mobility is experiencing a profound change. On the one hand, mobility patterns are becoming more complex, and typical home-work-home travel is no longer the rule, as journeys now tend to connect multiple points in a rather inconstant pattern. This has changed the approach to transport planning, in that the existing transportation planning and operation approaches have been focussed on the ability to identify typical home-work/school-home travel and subsequently plan the transport system accordingly. The traditional approach has been: forecast -> plan -> deliver, as new mobility solutions are emerging. These are characterised by greater flexibility, in that they take advantage of the “sharing concept” and simultaneously provide solutions that have lower GHG emissions. Urban mobility follows a fuzzier pattern, with even the urban transportation system behaving like an active organism, where solutions are often quickly replaced. This dynamic and evolving environment raises several new challenges at different levels. The best digital solution system is the Mobility-as-a-Service (MaaS) one. This system transforms the physical transportation system into a commodity and takes advantage of the internet of things (IoT). However, the onset of MaaS solutions is anything but linear. Several business models have emerged, with different partners originating from different industries (e.g., technological, transport operators, infrastructure managers, etc.) developing their own solutions, often in competition with others. It is not unusual to find different MaaS solutions in the same city, which integrate different solutions.