This paper discusses the state of the art in the application of self-healing silicone-based materials for outdoor high-voltage insulation. Both the dynamic behavior of the dimethyl side groups of silicone rubber and the diffusion of a bulk siloxane to maintain low surface energy are respectively reported as intrinsic mechanisms responsible for the self-healing of silicone rubber. Localization, temporality, mobility, and the type of synthesis are the aspects defining the efficiency of the self-healing ability of silicone rubber. In addition, the deterioration of the self-healing ability with filler loaded into silicone rubber insulation housing composites is discussed. Taking the self-healing property into consideration among the other properties of silicone rubber insulators, such as tracking and erosion resistance, can be a useful design practice at the material development stage. Hydrophobicity retention, recovery, and transfer measurements are discussed as useful indicators of the self-healing ability of silicone rubber. Nevertheless, there remains a need to standardize them as design tests at the material development stage. The paper is intended to shed the light on the hydrophobicity recovery, a key material design parameter in the development of silicone rubber outdoor insulating composites, similar to the tracking and erosion resistance.