Compared with water-based drilling fluids (WBDF), oil-based drilling fluids (OBDF) are more prone to borehole leakage loss. Once borehole leakage occurs, it’s difficult to handle the leakage site and it will inevitably cause great economic losses. To cope with the major difficulties in OBDF leakage-proof and crack plugging, this paper conducted experiments on an enhanced crack-plugging and pressure-bearing OBDF system starting from the borehole leakage prevention measures. Then, by selecting and optimizing the materials of leakage-proof agent and crack-plugging agent for OBDF, this study prepared a new-type OBDF drilling leakage-proof agent and a new-type OBDF still crack-plugging agent and discussed their action mechanisms. Laboratory experiment and mechanism analysis results showed that, a well-proportioned combination of different type OBDF leakage-proof and crack-plugging materials such as rigid bridging particles, elastic filling particles, and fiber materials had a synergistic plugging effect and quickly formed a dense crack-plugging and pressure-bearing layer with a stable network structure (the "strong-force chain network" model), which had significantly improved the crack-plugging and pressure-bearing performance of the OBDF, and further optimized the enhanced crack-plugging and pressure-bearing OBDF system; before and after the heated rolling aging, the rheological properties and filtration loss performance of the system were good, and the filtration loss of the sand filter cake of the Permeability Plugging Apparatus (PPA) was only 11.4mL, therefore, the proposed agents exhibited good performance in drilling leakage-proof, crack-plugging, and pressure-bearing, and they were helpful to improve the pressure bearing ability of the earth stratums.