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So it ended up being the most obvious place oil might leak from - drain plug. So after changing the gasket TWICE (two fresh ones), I have concluded it is not the gasket improperly seating and something with either the oil pan or the bolt itself. From the looks of it, there are no cracks in the oil pan and the drain plug seems to have no cracks in it either. Now I usually know what a stripped thread feels like but is this somehow a possibility? Like the threads are all boogered up but I can still torque it down? I'm honestly lost on this and if all else fails I guess I'll have to replace the oil pan?
P.S - At this point I don't feel like doing any shade tree fixes like putting crap on the threads to stop it from leaking, putting in a bigger sized plug, etc.
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