In Extraordinary Optical Transmission (EOT), a metallic film perforated with an array of [periodic] apertures exhibits transmission over 100% normalized to the total aperture area, at selected frequencies. EOT devices have potential applications as optical filters and as couplers in hybrid electro-optic contacts/devices. Traditional passive extraordinary optical transmission structures, typically demonstrate un-normalized transmission well below 50%, and are typically outperformed by simpler thin-film techniques. To overcome these limitations, we demonstrate a new breed of extraordinary optical transmission devices, by “burying” an extraordinary optical transmission grating in a dielectric matrix via a metal-assisted-chemical etching process. The resulting structure is an extraordinary optical transmission grating on top of a dielectric substrate with dielectric nano-pillars extruded through the grating apertures. These structures not only show significantly enhanced peak transmission when normalized to the open area of the metal film, but more importantly, peak transmission greater than that observed from the bare semiconductor surface. The structures were modeled using three-dimensional rigorous coupled wave analysis and characterized experimentally by Fourier transform infrared reflection and transmission spectroscopy, and the good agreement between the two has been demonstrated. The drastic enhancement of light transmission in our structures originates from structuring of high-index dielectric substrate, with pillars effectively guiding light through metal apertures.