This study investigates the variability of the seasonal cycle of convection in the Brazilian Amazon basin during the last decades, and examines physical mechanisms that potentially trigger these modifications. A new methodology to evaluate the onset and length of the rainy season using long-term cloud fraction observations from geostationary satellites is proposed and the connection between cloud cycle variability, surface properties, and thermodynamic and dynamic conditions is explored. The results show that cloud cover has significantly decreased over the last decades. The decline in cloudiness is steeper at 1200 UTC (0800 LT), when a trend of up to −6% decade⁻¹ is observed over the central and eastern Amazon. High-cloud-cover reduction is the major contributor to the observed decline in total cloud fraction. Delayed onsets and a reduction of up to 4 days yr⁻¹ in the northern and central Amazon wet-season length are observed. Correlation analyses indicate that the El Niño phenomenon affects the interannual variability of cloudiness in the Amazon, leading to delayed onset and early demise of the rainy season. The tropical South Atlantic, the Pacific warm pool, and the North Atlantic tripole also play a small, but significant, role in the Amazon’s cloudiness variability. The decrease in cloudiness over the Amazon basin reduces the amount of solar radiation reflected back to space while increasing irradiance at the surface. This local warming alters surface heat fluxes and the atmospheric thermodynamic profile, further affecting cloud development. The strong tendencies reported here indicate a significant shift in the Amazonian hydroclimate during the last few decades.