Plant-herbivore interactions have been extensively studied in tomato plants and their most common pests. Tomato plant chemical defenses, both constitutive and inducible, play a role in mediating these interactions. Damaged tomato plants alter their volatile profiles, affecting herbivore preferences between undamaged and damaged plants. However, previous studies on tomato volatiles and herbivore preferences have yielded conflicting results, both in the volatile chemistry itself as well as in the attraction/repellent herbivore response. This study revisits the volatile-mediated interactions between tomato plants and two of their main herbivores: the leafminer Tuta absoluta and the whitefly Trialeurodes vaporariorum. Tomato plant volatiles were analyzed before and after damage by each of these herbivores, and the preference for oviposition (T. absoluta) and settling (T. vaporariorum) on undamaged and damaged plants was assessed both after conspecific and heterospecific damage. We found that both insects consistently preferred damaged plants over undamaged plants. The emission of herbivore-induced plant volatiles (HIPVs) increased after T. absoluta damage but decreased after T. vaporariorum damage. While some of our findings are in line with previous reports, T. absoluta preferred to oviposit on plants damaged by conspecifics, which differs from earlier studies. A comparison of HIPVs emitted after damage by T. absoluta and T. vaporariorum revealed differences in up- or down-regulation, as well as significant variations in specific compounds (12 for T. absoluta and 26 for T. vaporariorum damaged-plants). Only two compounds, ß-caryophyllene and tetradecane, significantly varied because of damage by either herbivore, in line with the overall variation of the HIPV blend. Differences in HIPVs and herbivore preferences may be attributed to the distinct feeding habits of both herbivores, which activate different defensive pathways in plants. The plant's challenge in simultaneously activating both defensive pathways may explain the preference for heterospecific damaged plants found in this study, which are also in line with our own observations in greenhouses.