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oil leak 2008 softail

What did the old o-ring look like? I look at the o-ring that came out, if it is torn up pretty bad, I look to see if the is a burr or dirt tearing it up. Make sure the surface is clean. I also use the loctite 565 thread sealant.
 
I would check to see if cover has a small crack. If this is the case it may be able to be repaired, if not it will have to be replaced. Also check the threads in the cover as well as the plug itself. If it is the cover, you may be able to re-thread it, if it is the plug. just replace it. Teflon tape can be used as a short term fix. Hope this helps and good luck.
 
It should seal with the new "O" ring but if it doesn't like said above check for a crack in the case or add some thread sealant to the plug threads and see if that does the trick.
 
The drips of oil dropping from the primary drain plug may not be coming from the plug and as its the lowest point on the engine the oil may well be coming from elsewhere

Brian
 
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