In response to herbivory, plants emit specific blends of herbivore-induced plant volatiles (HIPVs). HIPVs mediate sizable arrays of interactions between plants and arthropods, microorganisms, undamaged neighboring plants or undamaged sites within the plant in various ecosystems. HIPV profiles vary according to the plant and herbivore species, and the developmental stages and conditions of the live plants and herbivores. To understand the regulatory mechanisms underling HIPV biosynthesis, the following issues are reviewed here: (i) herbivore-induced formation of plant volatile terpenoids and green leaf volatiles; (ii) initial activation of plant responses by feeding herbivores; and (iii) the downstream network of the signal transduction. To understand the ecological significance of HIPVs, we also review case studies of insect–plant and inter-/intraplant interactions mediated by HIPVs that have been documented in the field and laboratory in recent years.