Structural evolution of monsoon clouds in the core monsoon region of India has been examined using multisensor data. Invigoration of warm clouds above 4.5 km (occurring in only 15.4% days of the last 11 monsoon seasons) is associated with a transition from negative to positive normalized rainfall anomaly. Cloud top pressure reduces with an increase in aerosol optical depth at a higher rate of invigoration in drier condition (characterized by large fraction of absorbing aerosols) than wet condition. Cloud effective radius for warm clouds does not show any significant change with an increase in aerosol concentration in the presence of high liquid water path, probably due to strong buffering role of meteorology. The structural evolution of monsoon clouds is influenced by both dynamic and microphysical processes that prolong the cloud lifetime, resulting in infrequent rainfall. Our results call for improved representation of aerosol and cloud vertical structures in the climate models to resolve this issue.