A fundamental understanding of how near-IR light propagates through sound and carious dental hard tissues is essential for the development of clinically useful optical diagnostic systems, since image contrast is based on changes in the optical properties of these tissues on demineralization. During the caries (decay) process, micropores are formed in the lesion due to partial dissolution of the individual mineral crystals. Such small pores behave as scattering centers, strongly scattering visible and near-IR light. The optical properties of enamel can be quantitatively described by the absorption and scattering coefficients, and the scattering phase function. Our aim is to measure the optical scattering behavior of natural and artificial enamel caries. Near-IR attenuation measurements and angular-resolved goniometer measurements coupled with Monte Carlo simulations are used to determine changes in the scattering coefficient and the scattering anisotropy on demineralization at . An ultra-high resolution digital microradiography system is used to quantify the lesion severity by measurement of the relative mineral loss for comparison with optical scattering measurements. The scattering coefficient increases exponentially with increasing mineral loss. Natural and artificial demineralization increases the scattering coefficient more than two orders of magnitude at , and the scattering is highly forward directed.