Cities have lots of opportunities due to infrastructure development and modern life. But this modern life comes with other inconvenient packages; the most concerning one is high and frequent traffic jams. This traffic congestion can affect the vehicle speed and can increase the pollutant emissions and fuel consumption. Even though traffic jams result from several factors, the most important one is the road condition. Road conditions are highly dependent on the intactness of the subsurface layers of the pavement. Recently, many cities have encountered a sudden failure of roads because of the formation of cavities and weak subsurface layers in the process of natural and human construction activities. Several such incidents are being reported in India; major events are a metro bus and car plunged into a crater in Chennai city, the collapse of an entire street in Hyderabad, and the natural sinking of wells and houses in the Western Ghats in Kerala and North Karnataka. Such cavities and weak zones are unavoidable in cities; at the same time, proper, timely investigation and treatments can minimize such cavities, cavity-related disasters, and traffic-related discomfort to the public by making resilient infrastructure. This paper summarizes several urban incidents and their consequences, followed by a discussion on various reasons how the weak zones form due to improper subsurface layer handling in cities and how it deteriorates road conditions, along with the mapping of a typical cavity in the city using integrated investigation approach for underground metro tunneling.