The reaction between isocyanate-terminated prepolymers and atmospheric moisture produces urea linkages and results in a hydrogen-bonded network of linear high molecular weight polymers with adhesive properties. This study describes the synthesis of isocyanate-terminated prepolymers and investigates the use of in situ infrared spectroscopy as a technique for monitoring the chemistry of the polymerization reaction kinetics. In situ FTIR was successfully used as a means to monitor the residual isocyanate levels and the extent of the polymerization reaction. Frequency dependent dielectric sensing (FDEMS) using a thin, planar sensor has been used to monitor the reaction kinetics by monitoring changes in the mobility of ions in the reacting medium. A direct correlation of the extent of prepolymer cure was found using the normalized FTIR isocyanate absorbance spectrum and FDEMS imaginary permittivity at 500 Hz for the duration of the cure cycle. The results of this investigation demonstrate that FDEMS is an effective online method to monitor the extent of moisture cure in the bulk as well as in a coating or adhesive bondline.