A disjunct population of red stringybark (Eucalyptus macrorhyncha) trees in South Australia is experiencing increasing amounts of dieback. Because the population is considered vulnerable to extinction, we investigated spatiotemporal vegetation changes, quantified the extent of dieback, and determined how topography influences dieback using aerial and satellite imagery. Classification of vegetation health status using hyperspectral aerial imagery indicated that 37% (accuracy = 0.87 Kappa) of the population was unhealthy and potentially experiencing dieback. When correlating this classification with a digital terrain model (DTM), the aspect and amount of solar radiation had the strongest relationship with the presence of unhealthy vegetation. PlanetScope satellite-derived, and spectral index-based analysis indicated that 7% of the red stringybark population experienced negative vegetation health changes during a five-year period (2017–2022), with positive vegetation health changes (9.5%) noted on pole-facing slopes. Therefore, our integrated remote sensing approach documented the extent and spatiotemporal dynamics of dieback, suggesting it could be applied in other studies. Topographical aspects exposed to high-solar radiation were particularly vulnerable to dieback, and pole-facing aspects demonstrated some recovery between droughts. The influence of topography and maps of vegetation health can be used to guide future management and restoration of the population.