The movement direction of propagating convective systems originating from both inland and offshore over the north coast of West Java in Indonesia is determined primarily by the prevailing wind. However, the role of a land-sea contrast and a rugged topography over southern West Java is also expected to affect propagating convective systems by increasing land-sea breezes and enhancing upward motion. These hypotheses are tested using a weather prediction model incorporating convection (up to 3 km height) to simulate the heavy rainfall event during 26–29 January associated with the 2002 Jakarta flood. First, we addressed the influence of land-sea contrast and topography on the local circulation, particularly in the area surrounding Jakarta, by replacing the inland topography over western Indonesia (96°–119°E, 17°S–0°) with a water body with an altitude of 0 m. We then compared the results of model simulations with and without topography. The results show that the main role of the topography here is enhancing the upward motion and generating a deep convective cloud in response to the land-based convective system during 26–27 January 2002, which then continuously and rapidly propagates offshore due to the cold pool mechanism. Furthermore, the land-sea contrast has a significant role in increasing sea breeze under the rapidness of the landward propagation system during 28–29 January 2002, which was strengthened by the gravity waves and resulted in early morning convection over coastal regions.