Measuring the relative apparent dielectric permittivity of the subsurface is an easy and inexpensive way to indirectly obtain the volumetric water content. Many of the instruments that measure the dielectric, specifically borehole ground penetrating radar, rely on the travel time of an electromagnetic wave through a moist soil. Through inversion of the travel time, the water content can be calculated provided the path over which the wave travels is known exactly. In traditional interpretations of water content, the travel path of the electromagnetic wave is assumed to be direct from the transmitting antenna to the receiving antenna, irregardless of the propagation velocity structure. A new analysis is presented for the interpretation of first arrival travel time measurements from borehole ground penetrating radar during zero-offset profiling that considers critically refracted ray paths. By considering critical refraction at interfaces between contrasting propagation velocities, the travel path becomes dependent upon the velocity structure. Several infiltration experiments were performed to test whether critical refraction occurs in the subsurface. The infiltrating water will change the velocity structure of the subsurface in a predictable manner The interpretations of travel time were then compared to predictions made with an unsaturated flow model and supporting instrumentation. It was found that when critical refraction was not considered, the volumetric water content was underestimated by up to 30%. Correcting for critical refractions, therefore, becomes an important step in properly characterizing the subsurface. The new analysis presented herein may improve our ability to use direct measurements in water resource management practices to assess water availability in semi arid regions.