Without knowing more about your rig (i.e. what type/model diesel engine), a fair guess would be along the lines of Jeep69’s reply. With diesel engines (more so than gasoline), if your exhaust lifter were not traveling its designed duration and lift you would see excess exhaust gases/cylinder pressure escaping through the rings on the compression stroke (upwards movement). During this type of malfunction, you will also see additional smoke in the exhaust (un-combusted diesel and it may look like oil or it may in fact be oil).The access pressure would exit the path of least resistance (i.e. the oil filler or the other cylinders that are in a different stroke position?). Since a diesel engine uses a much higher compression ratio than gasoline, blow-by (reverse in this case) can occur easily. Additionally, as mentioned by other members, you may have cylinder sleeve and/or ring damage.
You could try simply replacing the tippet (lifter), but your cam is likely worn down as well. Ideally, you would replace the cam and lifters all at the same time. Once you set your lash, you can check your compression ratio. Smart money would be on pulling the block and rebuilding since you’re pretty much a third of the way just by pulling the cam.