In this study, the wettability of a kerogen surface, a key component of shale reservoirs, is investigated by using molecular dynamics simulations. Specifically, we examined the impact of droplet size and morphology as well as surface roughness on the water contact angles. The findings highlighted that the contact angle dependency on the droplet size intensifies with increased rigidity of the surface. Conversely, as the surface becomes more flexible and rougher, it gains hydrophilicity. The higher hydrophilicity stems from the ability of water molecules to penetrate the kerogen corrugations and form more hydrogen bonds with heteroatoms, particularly oxygen. Notably, the contact angle of kerogen hovers between 65 and 75°, thereby crossing the transition from an underoil hydrophilic to an underoil hydrophobic state. Consequently, minor alterations in the kerogen nanostructure can dramatically alter the wetting preference between water and oil. This insight is of paramount significance for refining strategies in managing fluid interactions in shale reservoirs such as geological carbon storage or oil extraction.