DKI Jakarta is an urban area with a high population density during working hours, reached 219 people/ha in 2017. This population density encouraged change in green open space to be roads and high-rise buildings, as well as increased exhaust emissions from motorized vehicles. As a result, urban heat island phenomenon has emerged in several locations such as the Jagorawi Toll Road, Cempaka Putih, and Kemayoran. Efforts have been made to reduce and mitigate these impacts by implementing vertical greening system at the flyover structure in DKI Jakarta. However, the temperature in DKI Jakarta continued to rise reaching >41?C in 2019 as the highest record. The continuous increase in temperature proved that the implementation has not been maximized. This study was conducted for the purpose of identifying the benefits and challenges of vertical greening system implementation at the flyover structure and analyzing existing condition of the implemented vertical greening system at the flyover structure in DKI Jakarta. The method used to achieve those purposes was survey by questionnaire and interview, conducted to the provincial government of DKI Jakarta and vertical greening system contractors. The results of this study pointed that the government and contractors most agree on the aesthetic benefits from the social aspect and the challenges of the initial investment from the cost aspect. The implementation of vertical greening system at the flyover structure has been carried out in 14 different locations with the majority of the systems implemented were living walls.