Molecular dynamics simulations were used to characterize the wetting behavior of crystalline cellulose planes in contact with a thin oily film of oleic acid. Cellulose crystal planes with higher molecular protrusions and increased surface area produced stronger adhesion if compared to other crystal planes due to enhanced wetting and hydrogen bonding. The detailed characteristics of crystal plane features and the contribution of directional hydrogen bonding was investigated. Similarly, oleophilicity of the cellulose planes increased with the increase in surface roughness and number of directional hydrogen bonds. These results correlate with conclusions drawn from experimental studies such as adhesion of an ink vehicle on cellulose surface.