Leaf-compression fossils with insect feeding traces are unique in providing rich, direct evidence of two levels in a fossil food web. Plant-insect associations dominate terrestrial trophic interactions, emphasizing the need to understand their ecological and evolutionary history. This paper first discusses methods of recognizing insect herbivore damage on fossil leaves and quantifying fossil insect herbivory. By conducting an unbiased insect damage census, damage frequency (percent of leaves with insect feeding damage), percent of leaf surface area removed by insects, and damage diversity (the number of discrete damage morphotypes, or DTs, found on a fossil flora or individual host plant) can all be measured. Three examples of responses of past plant-insect trophic interactions to environmental stresses are examined. In the first case study, late Oligocene fossil floras from Ethiopia document forest response to local perturbation and key characteristics to recognize disturbance in the plant fossil record. The second case study considers the terrestrial ecosystem response to the catastrophic global perturbation at the Cretaceous–Paleogene boundary. In the third case study, the impact of past global warming events—including the Paleocene–Eocene Thermal Maximum—on insect herbivory is discussed. Productive avenues for further research include: insect damage studies conducted outside the North American Cretaceous and Paleogene, actualistic and taphonomic studies of insect herbivory, and tighter collaboration across paleobotany, paleoentomology, botany, and entomology.