It sounds like both o-rings need replacing, at a minimum. Check for possible nicks or abrasions that would damage the o-rings when you reassemble. I had to purchase a new lower tube for mine as previous "mechanics" had dented and bent it severely.

No need to drop the oil pan unless the grommet and lower o-ring are so severely hardened that some of the chunks fall in when you remove the lower tube. Do you know how to tie a clove hitch? I just tied a couple of clove hitches around the lower tube with light rope then wrapped the other end around a large pry bar. Found a judicious spot to pry upwards and it popped out very easily.

I've seen other methods, including the hose clamp, but they all seemed to run the risk of damaging the lower tube. Besides, a couple of clove hitches is multiple times easier!

I believe there is thread where someone mentions changing out the o-rings and grommet in 10 minutes. Even with the engine in the car, it shouldn't take more than 30 min. with clean-up. If it does, you might be doing something the hard way.

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Sam

84 300SD 350K+ miles ( Blue Belle )