The Municipality of Turin has developed a strategic plan for the evolution of currently available ITS services towards the “Cooperative” model (C-ITS). A relevant task is the implementation of core technologies for Vehicle-to-Infrastructure communications (V2I). This paper describes two of the City’s main initiatives focusing on connected, cooperative and automated mobility, the “Torino Smart Road” and “C-ROADS Italy 2” projects. 5T is in charge of deploying those C-ITS services on the behalf of the Municipality, also in cooperation with Links Foundation research centre. In this paper, an overview is provided for both the mobility scenarios in Turin and the existing ITS services. The C-ITS deployment activities are summarized, as well. Finally, an account is given of the prototypal implementation of a roadwork warning C-ITS service and the major technical challenges, in particular concerning the matching between DATEXII and C-ITS messaging and the implementation of a “hybrid” 5G cellular/short-range communications infrastructure.