The global increase in observed forest dieback, characterized by the death of tree foliage, heralds widespread decline in forest ecosystems. This degradation causes significant changes to ecosystem services and functions, including habitat provision and carbon sequestration, which can be difficult to detect using traditional monitoring techniques, highlighting the need for large-scale and high-frequency monitoring. Contemporary developments in the instruments and methods to gather and process data at large scales mean this monitoring is now possible. In particular, the advancement of low-cost drone technology and deep learning on consumer-level hardware provide new opportunities. Here, we use an approach based on deep learning and vegetation indices to assess crown dieback from RGB aerial data without the need for expensive instrumentation such as LiDAR. We use an iterative approach to match crown footprints predicted by deep learning with field-based inventory data from a Mediterranean ecosystem exhibiting drought-induced dieback, and compare expert field-based crown dieback estimation with vegetation index-based estimates. We obtain high overall segmentation accuracy (mAP: 0.519) without the need for additional technical development of the underlying Mask R-CNN model, underscoring the potential of these approaches for non-expert use and proving their applicability to real-world conservation. We also find that color-coordinate based estimates of dieback correlate well with expert field-based estimation. Substituting ground truth for Mask R-CNN model predictions showed negligible impact on dieback estimates, indicating robustness. Our findings demonstrate the potential of automated data collection and processing, including the application of deep learning, to improve the coverage, speed, and cost of forest dieback monitoring.