A waste heat recovery system includes a Rankine cycle (RC) circuit having a pump, a boiler, an energy converter, and a condenser fluidly coupled via conduits in that order, to provide additional work. The additional work is fed to an input of a gearbox assembly including a capacity for oil by mechanically coupling to the energy converter to a gear assembly. An interface is positioned between the RC circuit and the gearbox assembly to partially restrict movement of oil present in the gear assembly into the RC circuit and partially restrict movement of working fluid present in the RC circuit into the gear assembly. An oil return line is fluidly connected to at least one of the conduits fluidly coupling the RC components to one another and is operable to return to the gear assembly oil that has moved across the interface from the gear assembly to the RC circuit.