Urban drought is an emerging challenge in rapidly growing cities, particularly under increasing climate variability and rising water demand. This study investigates urban drought dynamics across three secondary Indian cities namely Kozhikode, Bhuj, and Bhopal representing humid tropical, arid, and semi-arid climatic regions, respectively. Research delves into the analysis of drought using essential drought indices, including the Standardized Precipitation Index (SPI), Reconnaissance Drought Index (RDI), Departure Analysis of Rainfall (DAR), and Rainfall Anomaly Index (RAI) using DrinC software. Analysing 37 years of data, from 1984 to 2020, has provided invaluable insights into the trends and alterations in drought occurrences and rainfall patterns across these regions. Distinct disparities were revealed among these areas, notably the SPI values showing wet and dry periods. For instance, while Kozhikode experienced mild wetness during 2018-2019, Bhuj and Bhopal faced severe and extreme wetness, respectively, during similar time frames. Long-term rainfall pattern analysis unveiled fluctuations in precipitation concentration. The RDI values, spanning a considerable time frame from 1984 to 2020, indicate fluctuations in drought intensity over the years. The findings underscore that urban drought is not merely a hydrometeorological challenge but a multi-dimensional governance issue requiring systemic, cross-sectoral interventions. Beyond drought characterization, the study integrates drought diagnostics with Water-Sensitive Urban Design (WSUD) principles to explore governance pathways for improving urban drought resilience. The study also proposes a transitional framework that promotes decentralized water management, aquifer recharge, green-blue infrastructure, and participatory planning to strengthen long-term urban water resilience.