Flammability is a major factor involved in Mediterranean plant evolution that has led to the diversity of fire-related traits according to fire regimes and fire-adaptive strategies. With on-going climate change, new fire regimes are threatening plant species if they do not adapt or acclimate. Studying flammability and terpene content variation according to the different fire frequencies in the recent fire history represents a great challenge to anticipating the flammability of ecosystems in the near future. The flammability of shoots and litter as well as the needle terpene contents of two pine species with different fire adaptive strategies (Pinus halepensis and Pinus sylvestris) were measured according to two fire modalities (0 vs. 1–2 fire events over the last 60 years). Results showed that, regardless of the species and the fuel type, flammability was higher in populations having undergone at least one past fire event even when factors influencing flammability (e.g., structural traits and hydric content) were considered. The terpene content did not vary in P. sylvestris’ needles according to the fire modality, but that of sesqui- and diterpenes was higher in P. halepensis’ needles sampled in the “Fire” modality. In addition, associations made between flammability and terpene content using random forest analyses indicated that the terpene molecules differed between fire modalities for both species and fuel types. The same results were obtained with significant terpenes driving flammability as were highlighted in the PLS analyses, especially for P. halepensis for which enhanced shoot flammability in the “Fire” modality agreed with the adaptive strategy of this species to fire.