The present study focused on the Permian to Jurassic sequence in the Northern Highlands area, NW Jordan. The Permian to Jurassic sequence in this area is thick and deeply buried, consisting mainly of carbonate intercalated with clastic shale. This study integrated various datasets, including total organic carbon (TOC, wt%), Rock-Eval pyrolysis, visual kerogen examination, gross composition, lipid biomarkers, vitrinite reflectance (VRo%), and bottom-hole temperature measurements. The main aim was to investigate the source rock characteristics of these strata regarding organic richness, kerogen type, depositional setting, thermal maturity, and hydrocarbon generation timing. The Permian strata are poor to fair source rocks, primarily containing kerogen type (KT) III. They are immature in the AJ-1 well and over-mature in the NH-2 well. The Upper Triassic strata are poor source rocks in the NH-1 well and fair to marginally good source rocks in the NH-2 well, containing highly mature terrestrial KT III. These strata are immature to early mature in the AJ-1 well and at the peak oil window stage in the NH-2 well. The Jurassic strata are poor source rocks, dominated by KT III and KT II-III. They are immature to early mature in the AJ-1 well and have reached the oil window in the NH-2 well. Biomarker-related ratios indicate that the Upper Triassic oils and Jurassic samples are source rocks that received mainly terrestrial organic input accumulated in shallow marine environments under highly reducing conditions. These strata are composed mostly of clay-rich lithologies with evidence of deposition in hypersaline and/or stratified water columns. 1D basin models revealed that the Upper Triassic strata reached the peak oil window from the Early Cretaceous (~80 Ma) to the present day in the NH-1 well and from ~130 Ma (Early Cretaceous) to ~90 Ma (Late Cretaceous) in the NH-2 well, with the late stage of hydrocarbon generation continuing from ~90 Ma to the present time. The present-day transformation ratio equals 77% in the Upper Triassic source rocks, suggesting that these rocks have expelled substantial volumes of hydrocarbons in the NH-2 well. To achieve future successful hydrocarbon discoveries in NW Jordan, accurate seismic studies and further geochemical analyses are recommended to precisely define the migration pathways.