A direct interrogation, portable analysis technique (portable FT-IR) and a novel environment-monitoring profluorescent sensor for studying aircraft coating degradation have been developed. For the direct interrogation approach, a standard military aircraft paint: 459-line Anzothane flexible polyurethane (lead free) has been used to illustrate a new potential field technique to evaluate coating service lifetime, portable FT-IR. This technique allows direct analysis of chemical changes within the degrading coatings and has the potential to evaluate service lifetime when coupled with advanced statistical analysis methods (chemometrics). The degradation environment monitoring sensors are embodied in a profluorescent environment-sensitive witness patch that may be analysed in-service by a field-deployable fluorescence spectrometer. Accelerated ageing for both the paint and the witness patches has been undertaken and their capabilities as aircraft paint degradation monitors assessed.