In recent years, the anomalous transmission of subwavelength apertures has become an emergent subject within the physical sciences. While the gain mechanism of these structures is still uncertain, the effect has been observed in several studies. Similar transmission enhancements may be realized for near-wavelength sized photomask structures by including buried grooves in a dual write mask design. Several configurations of one-dimensional transmitting apertures and buried grooves have been investigated under TM illumination using the finite element method. Periodic subwavelength apertures with identical sized nontransmitting assist grooves were used to validate the model against reference data in the near-IR. The method was also used to investigate similar structures featuring a larger than wavelength transmitting aperture. Although transmission through the slot was increased by 1.67x, the primary lithographic benefit was an increase in the magnitude of the primary imaging orders relative to the zeroth diffracted order. A similar approach was extended to structures scaled to 248 nm to show application as a potential lithographic assist feature. A 5.7x transmission increase was observed using aluminum on fused silica configuration using 30 nm slots on a 192 nm pitch.