The rapid development of the digital age can change almost every aspect of modern life. With the advancement of technology, all can be done more easily. This creates a concept called "Smart City" where all the things that people do everyday in the city become integrated and sustainable by technology. Currently in Indonesia all business sectors have entered an era where digital platform plays an important role in it, PT Railink is one of them, PT Railink as a new provider of airport rail services issued online ticketing service based on smartphones, which of course aims to facilitate consumers to be more convenient to book the airport train tickets, but currently Railink application may not be widely accepted by the users of this service. This study focuses on measuring the acceptability of technology in Railink applications by using TAM and TRA modifications based on the SEM methodology. This research was conducted in Jakarta with two study materials, which are X and Y generations society. The result of research shows high positive impression felt about the usefulness and easiness for both generations. Analysis of technology adoption lifecycle and technology roadmaping shows that Railink application has been adopted by early majority and late majority. This indicates that the Railink app is in the ascent and mature stages, so it's important for application developers to continue promoting in order to attract more X generation to use Railink application, and for Y generation, developers should keep updating features, and make a loyalty points for the Y generation to continue using the Railink application for the next 5-10 years.