Twenty six samples of Permian high latitude sedimentary rocks from the southern Sydney Basin were analysed using organic geochemical methods for their thermal maturity, organic matter inputs, and depositional environment. Fourteen samples are from the Elecom Clyde River (ECR) DDH01 borehole (inland; Southern Highlands), and 12 are from the ECR-DDH07 borehole (coastal; near Nowra). The analysed formations are the Berry Siltstone, the Nowra Sandstone, the Wandrawandian Siltstone, the Snapper Point Formation and the Pebbley Beach Formation. This study is the first organic geochemical study of samples from the Berry Siltstone and Nowra Sandstone. The formations mostly have total organic carbon varying from 1 to 2 wt%, but the Snapper Point Formation is leaner in TOC (0.2–0.7 wt%). The samples vary from low to very high thermal maturity. The samples from the ECR-DDH01 borehole are in the early to middle of the oil window (vitrinite reflectance equivalent = 0.60–0.80%), based on hopane, sterane, alkylnaphthalene, alkylphenanthrene, alkylbiphenyl, and alkyldibenzothiophene thermal maturity parameters. The samples from the ECR-DDH07 borehole are much more thermally mature, in the late part of the oil window to the early gas window (vitrinite reflectance equivalent = 1.2–1.7%). This high thermal maturity has led to the loss of nearly all polycyclic biomarkers, and the thermal rearrangement of many groups of compounds, including monomethylalkanes. The ECR-DDH01 borehole location and time-equivalent outcrop samples south-west of Ulladulla have similar thermal maturities and are close to the margins of the Sydney Basin, and it is estimated to have previously been covered by about 3 km of overburden. In contrast, the samples in the ECR-DDH07 borehole were buried much deeper, with about 4–5 km of overburden, which means that only limited information about their source inputs and depositional environment could be recovered. Aliphatic biomarker, n-alkane and aromatic data are consistent with an overall strong terrigenous organic matter input for the samples from the ECR-DDH01 borehole. Sterane/hopane ratios are mostly low, but only a few compounds diagnostic of specific source inputs were identified. There is a microbially-dominated sample near the base of the Snapper Point Formation (high C29 αβ hopane/C30 αβ hopane ratio and 2α-methylhopanes), and high amounts of parent polycyclic aromatic hydrocarbons in some samples from the Berry Siltstone, likely reflecting an occasional pyrogenic signature from palaeo-forest fires. Several parameters, including sterane carbon number distributions, terpane ratios and the relative abundance of dibenzofuran compared to phenanthrene show that the samples from the ECR-DDH01 borehole have a more strongly terrigenous signal than the previously analysed outcrop samples. This is inferred to be because the ECR-DDH01 location was closer to the palaeo-shoreline than the likely more distal outcrop samples. Based on the pristane/phytane ratio and hopane distributions, deposition of the sediments was under varying oxicity conditions, from highly oxic to suboxic. The inferred environments are marine shale/lacustrine and fluvial/deltaic, so the organic geochemical data agrees with the Permian depositional history of the southmost part of the Sydney Basin previously inferred from sedimentological and palaeogeographic studies.