In primates, the putamen and the caudate nucleus are connected by ∼1mm-thick caudolenticular gray matter bridges (CLGBs) interspersed between the white matter bundles of the internal capsule. Little is understood about the functional or microstructural properties of the CLGBs. In studies proposing high resolution diffusion magnetic resolution imaging (dMRI) techniques, CLGBs have been qualitatively identified as an example of superior imaging quality, however, the microstructural properties of these structures have yet to be examined. In this study, it is demonstrated for the first time that diffusion MRI is sensitive to an organized anisotropic signal corresponding to the CLGBs, suggesting that diffusion MRI could be a useful imaging method for probing the unknown microstructure of the CLGBs. In addition, a novel tractography algorithm is proposed that utilizes the shape of the human striatum (putamen + caudate nucleus) to reconstruct the CLGBs in 3D. The method is applied to three publicly available diffusion imaging datasets varying in quality and thereafter demonstrating that the reconstructed CLGBs directly overlap expected gray matter regions in the human brain. In addition, the method is shown to accurately reconstruct CLGBs repeatedly across multiple test-retest cohorts. Finally, by using the CLGB reconstructions and a local model of the diffusion signal, a method is proposed to extract a quantitative measurement of microstructure from the CLGBs themselves. This is the first work to comprehensively study the CLGBs in-vivo using diffusion MRI and presents techniques suitable for future human neuroscience studies targeting these structures.