Rail seat deterioration (RSD) is the most critical problem with concrete tie performance on North American freight railroads. Currently, the problem is not sufficiently understood to allow for effective solutions. RSD is considered to have up to five potential mechanisms, and this paper investigates one of them: hydraulic pressure cracking. A model of the effective stress in a concrete tie rail seat -considering the contributions of a uniform vertical load, a uniform lateral load, a prestressed beam on an elastic foundation, and pore pressure to the state of stress - was created to determine what surface water pressures at the rail seat could lead to damaging pore water pressures in the concrete. A laboratory test setup and procedure were devised to measure the surface water pressure in a laboratory rail seat using tie pads of differing material composition and geometry. Results show that the magnitude of the pressure generated and the rate of pressure dissipation with many load cycles depends on the pad material and surface geometry. Comparing the effective stress model and the measured surface pressures, hydraulic pressure cracking appears to be a feasible mechanism for RSD given the correct combination of dynamic rail seat loads, sufficient moisture, and a tie pad surface that develops high pressure.