The Paleozoic-Mesozoic transition is characterized by the most massive extinction of the Phanerozoic. Nevertheless, an impressive adaptive radiation of herbivorous insects occurred on gymnosperm-dominated floras not earlier than during the Middle to Late Triassic, penecontemporaneous with similar events worldwide, all which exhibit parallel expansions of generalized and mostly specialized insect herbivory on plants, expressed as insect damage on a various plant organs and tissues. The flora from Monte Agnello is distinctive, due to its preservation in subaerially deposited pyroclastic layers with exceptionally preserved details. Thus, the para-autochthonous assemblage provides insights into environmental disturbances, caused by volcanic activity, and how they profoundly affected the structure and composition of herbivory patterns. These diverse Middle Triassic biota supply extensive evidence for insect herbivore colonization, resulting in specific and complex herbivory patterns involving the frequency and diversity of 20 distinctive damage types (DTs). These DT patterns show that external foliage feeders, piercer-and-suckers, leaf miners, gallers, and oviposition culprits were intricately using almost all tissue types from the dominant host plants of voltzialean conifers (e.g., Voltzia),horsetails, ferns (e.g., Neuropteridium, Phlebopteris, Cladophlebis and Thaumatopteris), seed ferns (e.g., Scytophyllum), and cycadophytes (e.g., Bjuvia and Nilssonia).