The increased occurrences of drought and fire may be contributing to the loss of biodiverse ecosystems in Mediterranean regions. Specifically, the conversion of diverse native shrublands, such as chaparral, to non-native annual grassland by fire is of great conservation concern in California. To avoid or slow the loss of chaparral, it is important to understand the underlying causes of landscape conversion. Studies investigating the interaction of multiple potential drivers are particularly crucial to identification of vulnerable areas of the landscape.Here we used aerial imagery to evaluate vegetation transitions between chaparral, sage scrub, grassland, and tree domination and their potential drivers within Ventura County, CA, a strongly Mediterranean climate region. We used random forest algorithms and conditional inference trees to determine the climatic, topographic, and fire-related variables contributing most to vegetation change. Our results support that chaparral conversion to grass (27% of chaparral plots) is a result of landscape position, fire, and drought acting in tandem. In particular, lower elevation, southwest-facing slopes that experience a postfire drought are at very high likelihood of conversion to non-native annual grass. Additionally, our results show that these grasslands, once formed, rarely convert to other community types. Therefore, protecting shrub-dominated areas that are most likely to convert (low elevation, more southwest-facing slopes, and less annual precipitation) is crucial to preserving native vegetation diversity.