The development of information technology had a major impact on human life. The impact has touched various aspects including the world of transportation.The need for larger modes of transportation is accompanied by people’sincreased mobility, which is not supported by government readiness to provide cheap, safe, comfortable and affordable modes of transportation. In the implementation of transportation system, on-line application-based transport modes that targeted taxi and motorcycle markets emerged. This online transportation has been presencethroughout Indonesia, including in the Special Region of Yogyakarta. This research aims to expose the administration of online transportation and its obstacles in the Special Region of Yogyakarta.The research is an normative-empirical legal research using juridical approach with descriptivequalitative analysis. The primary data were collected through library review and field research as well as indepth interview with relevant resource persons. In its management, the Departement of Transportation as the regulator has authority in licensing and supervising of online transportation in the Special Region of Yogyakarta.Even though the government has given permission and conducted surveillance on online transportation in DIY, some obstacles are still faced in managing online transportation in the Special Region of Yogyakarta. These obstacles include,Government delays in providing adequate transportation in terms of quality and quantity and the absence of the Regulation of the Special Region of Yogyakarta governing online transportation. To resolve these conflicts,the researcher hope that the DIY government makes special regulations regarding online transportation.