Trento is a medium Italian city (circa 116.000 people) characterized by a modern service sector, a high quality of life, as well as by a quite consolidated innovation eco-system including a well-known University, Fondazione Bruno Kessler, several other research centres and many innovative companies and start-ups. Trento is working towards transforming itself into a Smart City and is already among the top smart-cities in Italy. In particular, the digitalization of all interactions between the PA and its citizens is a priority for Trento, and the city is currently working on a strategic project in this area. In the course of 2017 Trento has been committed in completing two major challenges: delivering the first version of Sportello Online, the selected solution for providing e-services to end users and making the provided e-services, integrated with the SIMPATICO features and tools, being used in a real environment by citizens and professionals. The introduction of Sportello Online was more complex than expected. The difficulties were both from the technical and the organizational sides. The clear roadmap of the steering team, the determination of the technical team and the involvement and collaboration of the Civil Servants were the factors that made it possible to achieve the desired results. Through Sportello Online the municipality has been able to deploy, test and evaluate two complex e-services (childhood enrollment and the acoustic derogation services), adding a third e-service in the last weeks of the experimentation (Landscape permit and mandatory opinions on the architectural quality of the interventions). The Sportello Online deployment has been the occasion also to evaluate the SIMPATICO tools in a real environment. In fact in Trento the SIMPATICO solution has been deployed as an extension of the Sportello Online digital module manager. All the features provided by the project have been made available to the final users. The integration was straightforward; one point that must be stressed is that there were no particular problems in extending the selected e-services in order to support SIMPATICO features. In Trento both the end users (citizens and professionals) and the civil servants were amazed of the Citizenpedia and the Workflow Adaptation features. Unfortunately the digital module turned out not to be the right place to evaluate the Text Adaptation techniques which have not been really used as expected by citizens and professionals; on the other side the potential of the Text Authoring feature has been well understood by civil servants. During the evaluation period more than 80 users (citizens and professionals)used the delivered e-services. We can say that, both from the documentation presentation and the digital module management, the Sportello Online powered with SIMPATICO features deployment has been well accepted from citizens, professionals and civil servants. The success, if possible, fostered the motivation of Trento steering and technical team in pushing the delivery of all the services provided by the municipality in the digital format. Beside the technical and organization challenges, this in perspective means to find a solution for supporting Sportello Online powered with SIPATICO features beyond the duration of the project.