The current study deals with the prediction of weather-related alterations of physicochemical properties and resulting functional failures of water-borne exterior wood coatings to reduce testing periods and development expenses for the respective materials. For that, structural and functional alterations of natural and artificial weathered wood coatings were monitored using both well established analytical and material testing tools (e.g., FTIR spectroscopy, DSC, light microscopy, SEM, colorimetry, micromechanical analysis) and unconventional analytical methods such as UV-GC/MS and chemiluminescence analysis which are new in the field of wood coatings characterization. Prediction models were obtained by linear modeling and multiple regression analysis of data sets from natural and artificial weathering cycles indicating 1) early occurring structural changes, 2) subsequent functional alterations/critical states and 3) functional breakdown of wood coatings.