To better characterize a bulk soil electrically, both the electrical conductivity and dielectric permittivity should be measured. This study developed a time domain reflectometry (TDR) penetrometer to allow simultaneous measurements of dielectric permittivity and electrical conductivity during cone penetration. A TDR penetrometer is formed by placing a multiple-conductor waveguide around a nonconducting shaft. Probe design considerations and calibration methods for measuring dielectric constant were first theoretically discussed and then evaluated through laboratory investigations. A prototype TDR penetrometer was fabricated and used to perform simulated penetration tests in a calibration chamber. The effect of penetration disturbance on dielectric constant is quantitatively reported and explained. The implications of the data that can be measured by the TDR penetrometer are also discussed.