In this study, the survival and growth of seven probiotic Lactobacillus pentosus strains isolated from Aloreña green table olives in the presence of vegetable-based edible oils (i.e., sunflower, olive, linseed, soy, corn, almond and argan) and mint essential oil were determined for the first time. Slight decreases in bacterial viability were observed depending on the strain and oil expsoure, mainly mint essential oil. However, pre-adapting the strains to the corresponding oils significantly increased their cell viabilities. As such, this study examined whether pre-adapting probiotic L. pentosus strains with oils will constitute a new strategy to increase stress resistance, e.g., acids (pH 1.5) or bile (up to 3.6%) in food production and/or during digestion, and improve functional probiotic properties. Improvements in stress resistance were noticed in some pre-adapted strains with oils, such as under acidic and bile conditions; further, pre-adaptations with olive, argan, sunflower and linseed oils induced gene expression (e.g., fus, rpsL, pgm, groEL, enol and prep) for moonlighting proteins involved in several stress responses and other functions. As such, pre-adaptation with vegetable edible oils may represent a novel approach for manufacturing probiotic products by improving the stability of bacteria during industrial processes that would otherwise reduce the viability and functionality of the strains.