The present invention discloses a reactivity-based self-stratifying coating composition. The coating composition can include a polyol, silsesquioxane, a polyester polyol, and a crosslinker that form a mixture within a solvent. The polyol can be selected from a fluorinated polyether, a fluoroethylene-alkyl vinyl ether and/or a combination thereof. The silsesquioxane can be an epoxy functional silsesquioxane having a formula of (R)6(C6H11O2)2(SiO1.5)8 where R can be selected from hydrogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, cyclopentyl, cyclohexyl, benzyl, phenyl, and isomers thereof. In some instances, the epoxy functional silsesquioxane can be a di-epoxy silsesquioxane.