The extraction of procyanidins from a food is influenced by food matrix, extraction solvent, sample particle size, sample to solvent ratio, as well as other factors. Many of these parameters can easily be controlled in a laboratory to improve or target the extraction of low or high molecular weight oligomers. As various oligomers have differing biological and functional qualities, preferred extraction of one group of oligomers may be a desired target. In the following study, we describe the influence of solvent polarity and composition, solvent-solute ratio and particle size on the extraction of procyanidin oligomers monomer through decamer. The solvents evaluated included dimethyl sulfoxide (DMSO), acetone and methanol.