Hard yet flexible coatings with a pencil hardness of 9H and an extremely low bending radius (r < 1 mm) are promising candidates for cover window surface-protective coatings for nextgeneration thinner foldable displays. However, the inherent conflict between hardness and flexibility hinders their development, rendering the preparation of such materials still a significant challenge. To address this inherent trade off, this study presents a simple and effective strategy for fabricating molecular composites with the desired properties. The composite was prepared through photoinitiated free radical polymerization, utilizing caged eight (methacrylate) silsesquioxane (MA-POSS) and caged eight (3mercaptopropyl) silsesquioxane (MP-POSS). The silica core of POSS imparted the necessary hardness, while the thiol groups on the side chains contributed to high flexibility through chemical cross-linking. Leveraging the excellent miscibility and versatility of the two POSS, we systematically regulated the composition and internal structure of the coating to achieve high transparency (95.9%, 550 nm), outstanding pencil hardness (9H), and excellent low modulus (2.53 GPa). When applied to a poly(ethylene glycol terephthalate) (PET) film, the coating not only withstood 1000 steel wool abrasion cycles but could also be repeatedly bent at least 1000 times (r ∼ 0.8 mm). Simultaneously, the introduction of high-dielectric-constant atomic sulfur increased the dielectric constant of the PET film cover window from 3.01 to 3.46. Additionally, surface modification of the final coating with fluorinated monomers (TFOA) imparted oil and water resistance without compromising other performance characteristics. This research introduces an approach to the development of surface-protective coatings for next-generation foldable displays.