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I had cross threaded the cap on my little Husky years back. Saw would leak most of the tank out when sitting for a while. You could barely tell the threads were messed up, and I probably wouldn't have noticed if I didn't do it myself. Couple bucks for a new cap, no more problem. Might be a cheap try to fix the issue.
My first guess would be the rubber gasket around the oil pump. Part #503 85 47-01
I replaced that oil pickup tube on my 353 because as near as I could tell it was leaking out around that tapered rubber part where it goes into the oil tank. it fixed the problem for me. I just try not to bring it in out of the cold to a warm shop, and if I do I try to remember to crack the cap so it doesnt build up pressure in there and push oil out. not sure if that is making the difference or not. but my saw doesnt leak anymore
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