The transport sector has been increasing rather than decreasing its CO2 emissions, and its sustainable electrification faces a number of technical and non-technical challenges. This paper investigates these challenges, namely those of the grid load demand modelling, renewables integration, the present infrastructure limitations, and the policy/non-technical challenges. In synthesis, the suggested vision for the future sustainable urban bus network is presented as a catenary grid running In-Motion-Charging trolleybuses, with integrated PV, EV chargers, and stationary storage systems. The future grid must involve external players such as the DSO/TSO and research/academic institutions, with a dedicated coordination body, from pre-tendering all the way to daily operations.