Among the important properties of silicone is hydrophobicity but one of the challenges associated with contact angle measurement is that it a macroscopic quantity and does not provide molecular insight into the material property. Better understanding the behavior of a silicone insulation material in its environment requires better characterization methods due to the multitude of molecular interactions involved. This presentation describes developments in regard to fundamental surface characterization of insulator materials exposed to chemical and biological stresses. It also explains that there are changes in the silicone surface as a result of environmental exposures that in the early stage are not detectable by contact angle measurements or even surface probes.