Urban flooding has emerged as one of the most pressing environmental challenges in Indian cities, particularly in rapidly urbanizing regions such as Hyderabad. This study examines the flood resilience and drainage challenges of two waterlogging-prone colonies Hafeezpet and LB Nagar. Frequent monsoon flooding in these localities disrupts daily life, damages property, and reveals significant gaps in the city’s stormwater management system. Data for this study were collected through field observations, structured interviews with residents, and secondary sources including GHMC reports and satellite imagery. Findings indicate that blocked drains, encroachments on natural waterways, and unplanned urban expansion are major causes of recurrent flooding. The study emphasizes the need for integrated urban water management, public awareness, and resilient infrastructure to mitigate future flood risks.