While the design of short and intermediate buildings is governed by strength/deflection, the governing design of tall buildings is wind-induced motion. This paper mainly presents the challenges faced in the design and construction of a 45-storey and a 75-storey tall residential building in Mumbai, India. Adoption of cruciform (shape) floor plan for the latter was found to improve the aerodynamic profile, thereby reducing the wind forces by 25–30%. Huge shear demands that exceeded the capacity of conventional coupling beams was overcome with the use of steel plate-reinforced composite coupling beams. Study on soil-structure interaction conducted to capture the actual soil behaviour, exhibited pile reactions lesser by as much as 10% compared to conventional analysis. A study on mock-up specimens of the massive tower foundations confirmed the adequacy of the concrete design mix, in terms of temperature gradient and peak temperature in concrete. Construction sequence analysis carried out to mitigate the effect of axial shortening of columns did not yield significant results probably due to the compressive stress and reinforcement ratio in the vertical elements being controlled, where possible. Pushover analysis, a non-linear static analysis method, is incapable of capturing higher modes of vibration (governing modes for tall buildings), which puts forth another challenge before engineers.