High levels of exhaust temperature or rich mixtures are necessary for the regeneration of today's diesel particulate filters or NOx catalysts. Therefore, late main injection or post injection is an effective strategy but leads to the well-known problem of lubricating oil dilution depending on the geometry, rail pressure and injection strategy. In this paper a method is developed to simulate fuel entrainment into the lubricating oil wall film in the diesel combustion chamber to predict oil dilution in an early design stage prior to hardware availability for durability testing. The simulation method integrates a newly developed droplet-film interaction model and is compared to results of an optical single-cylinder diesel engine and a similar thermodynamic single-cylinder test engine. Phenomena of diesel post injection like igniting early post injection or split post injections with short energizing times are considered in this paper. Fuel entrainment into the wall film increases with retarding post injection to a maximum of about 30 % of the fuel mass injected by post injection. Split post injections decrease this rate to almost zero but inject a significantly lower amount of fuel.