Soy milk is a highly stable emulsion mainly due to the presence of oleosomes, which are oil bodies and function as lipid storage organelles in plants, e.g., in seeds. Oleosomes are micelle-like structures with an outer phospholipid monolayer, an interior filled with triacylglycerides (TAGs), and oleosins anchored hairpin-like into the structure with their hydrophilic parts remaining outside the oleosomes, completely covering their surface (K. Hsieh and A. H. C. Huang, Plant Physiol., 2004, 136, 3427-3434). Oleosins are alkaline proteins of 15–26 kDa (K. Hsieh and A. H. C. Huang, Plant Physiol., 2004, 136, 3427–3434) which are expressed during seed development and maturation and play a major role in the stability of oil bodies. Additionally, the oil bodies of seeds seem to have the highest impact on coalescence, probably due to the required protection against environmental stress during dormancy and germination compared to, e.g., vertebrates' lipoproteins. Surface pressure investigations and Brewster angle microscopy of oleosomes purified from raw soy milk were executed to reveal their diffusion to the air–water interface, rupture, adsorption and structural modification over time at different subphase conditions. Destroying the surface portions of the oleosins by tryptic digestion induced coalescence of oleosomes (J. Tzen and A. Huang, J. Cell. Biol., 1992, 117, 327–335) and revealed severe changes in their adsorption kinetics. Such investigations will help to determine the effects behind oleosome stability and are necessary for a better understanding of the principal function of oleosins and their interactions with phospholipids.