Oak trees host an amazing diversity of insects, many of which specialize on Quercus species. Oak species and genotypes are commonly planted far from where an acorn was produced. Urban plantings, restoration sites, and plantings anticipating climate change each cause this to happen. What evidence exists that provenance of oak plantings affects herbivores such as galls and leaf miners? And what other factors, such as weather, predators, urban forestry, and geographic isolation affect the populations of these insects? I present evidence from studies of oaks conducted at different scales. Provenance matters to herbivores - but predominantly at large genetic scales. Aspects of the urban environment can help some herbivores of oak trees but hurt others. Predators are of key importance to populations of gall wasps and leaf miners, and isolated trees can maintain a great diversity of galls and miners. Creating habitat for oak herbivores (at least the ones that do not kill trees) can be a great benefit of planting native oaks, and many of those insects are nearly as charismatic as their host trees!