Direct searches for weakly interacting massive particles (WIMPs) are rapidly approaching the “neutrino fog,” where solar neutrinos become an irreducible background. Overcoming this limit requires directional sensitivity to distinguish dark matter-induced nuclear recoils from neutrino events. Towards this goal, we are developing a diamond-based directional detector, where nuclear recoils generate ~10-100 nm damage tracks that can be identified and reconstructed using nitrogen-vacancy (NV) quantum sensors. I will describe recent advances toward this goal, including the detection of single-ion-induced damage tracks in nitrogen-rich diamond, the development of light-sheet quantum diamond microscopy for volumetric strain imaging, and progress in modeling recoil cascades with ML-accelerated molecular dynamics. In addition, I will report preliminary spin measurements on NVs associated with recoil tracks, which may provide a basis for quantum-sensing-assisted track discrimination. Taken together, these results illustrate a path forward towards a scalable, directional dark matter detector capable of probing beyond the neutrino fog.