Forest insects are among the most important factors of disturbance in European forests. The increase in and duration of drought stress events due to climate change not only increase the vulnerability of rural and urban forests but also predispose weakened stands to insect pest calamities. In this context, many German and European forest research institutes and environmental institutions report an increase in the densities and calamity developments of the oak processionary moth (Thaumetopoea processionea L.) not only in oak and mixed-oak forests but also in smaller areas where oak trees regularly occur, e.g., parklands, urban areas, copses, avenues, recreational forests, etc. It is expected that the oak processionary moth (OPM) will benefit from the overall weakened vitality of both individual oaks and oak stands in the future and that mass outbreaks will occur at an increased frequency. This paper reports on the effects that the OPM can have on tree performance for rural forest and urban oak trees by applying the chlorophyll fluorescence non-destructive diagnostic method for the identification and quantification of damage to oak leaves. The aim of the study was to investigate the effects of OPM frass activity on tree leaf health using chlorophyll fluorescence measurements, comparing infested host oaks with non-infested oaks in urban and forest environs. The study assessed: 1. the quantum efficiency of photosystem II (PS II), which counts as an indicator for leaf conditions, 2. the performance index, which indicates the efficiency of the photosynthetic light reaction, 3. the energy loss of the photosynthetic reaction, which is an indicator for cell damage, and 4. the degree of open reaction centers in PS II, which indicates how well light energy can be absorbed for photosynthesis. Infested urban and rural oaks showed a significantly reduced quantum yield of PS II by up to 10% compared to non-infested oak leaves. The leaf performance was significantly reduced by up to 35% for infested urban oaks and by up to 60% for infested forest oaks, respectively. The energy losses were two times higher for infested urban and forest oaks. However, OPM infestation led to a higher reduction in the photosynthetic performance in the leaves of forest oaks compared to that of urban oaks. In order to avoid permanent damage, suitable countermeasures must be taken quickly, as, immediately after pest infestation, the performance decreases significantly. A lower performance means a significant loss in biomass production as well as in tree vitality.