Current climate and land cover change threaten global mountaintops with increased spread of invasive species. Long-established plantations of invasive trees on these mountaintops can alter their surroundings, further increasing invader-facilitated invasion. Identifying the ecological conditions promoting such associations can help develop better management interventions. The Western Ghats's Shola Sky Islands (>1400 m MSL) host vast stretches of invasive tree plantations that sustain the colonization of other invasive woody, herbaceous, and fern species in their understories. Here, we analyzed vegetation and landscape variables from 232 systematically placed plots in randomly selected grids using non-metric multidimensional scaling and Phi coefficient approaches to examine patterns of association (positive interactions) between understory invasive species with specific invasive overstory species. We also conducted GLMM with zero inflation to determine the influence of environmental variables where such associations occur. We find that understory invasion of multiple species under the canopy of other invasives is widespread across the Shola Sky Islands. Stands of host the colonization of 70% of non-native invasive species surveyed across the Shola Sky Islands. In particular, the invasion is strongly associated with stands. We also found that climatic variables affect the colonization of understory woody invasive species, while invasion by exotic herbaceous species is associated with the density of road networks. Canopy cover impacts all invasives negatively, while fire incidence was negatively associated with invasion by spp. and the spp. While the restoration of natural habitats primarily targets the highly invasive , less invasive and are often not included. Our study suggests that retaining such invasive species in natural habitats, particularly protected areas, can hinder ongoing grassland restoration efforts by facilitating further invasions by multiple woody and herbaceous species.