Widespread encroachment of the fire-intolerant species Juniperus virginiana L. into North American grasslands and savannahs where fire has largely been removed has prompted the need to identify mechanisms driving J. virginiana encroachment. We tested whether encroachment success of J. virginiana is related to plant species diversity and composition across three plant communities. We predicted J. virginiana encroachment success would (i) decrease with increasing diversity, and (ii) J. virginiana encroachment success would be unrelated to species composition. We simulated encroachment by planting J. virginiana seedlings in tallgrass prairie, old-field grassland, and upland oak forest. We used J. virginiana survival and growth as an index of encroachment success and evaluated success as a function of plant community traits (i.e., species richness, species diversity, and species composition). Our results indicated that J. virginiana encroachment success increased with increasing plant richness and diversity. Moreover, growth and survival of J. virginiana seedlings was associated with plant species composition only in the old-field grassland and upland oak forest. These results suggest that greater plant species richness and diversity provide little resistance to J. virginiana encroachment, and the results suggest resource availability and other biotic or abiotic factors are determinants of J. virginiana encroachment success.