Traditional performing arts are currently lack on interast in urban region, especially in Semenep City, Madura. However, for a long time, the traditional art like Ketoprak Rukun Karya more famous in outer islands of Madura and even in Java. This paper aims to trace the transnationalization of Ketoprak Rukun Karya in the outer islands of Madura and in parts of Java also. This research uses a historical method that have 4 stages, heuristic (collecting sources), criticism, interpretation (analysis and synthesis), and historiography. By using a transnational point of view and also perusing several offline and online sources, such as archives, newspapers, magazines, photos and videos, this paper find out that: since the last 2 decades, Ketoprak Rukun Karya has shown its existence outside Sumenep City. Urban modernization causes lack attention of millennial generation to this traditional art. Ketoprak Rukun Karya experiencing transnationalization to the outer islands of Madura, and even to Java. This ketoprak has a special mission in each of its performances, that is the cultural education.