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Well, draining oil in a SS there is no place for the oil to collect and fall to the ground at a later time. Oil filter is open no frame in the way. And of course the drain plug is open as well.
Could have the filter not tight enough I guess. But the underside not clean is probably not the problem. Could be that whomever changed the oil spilled while pouring the new oil in up top.
Some here had oil leak from oil cooler and/or pan gasket. I would crawl under and see for myself. Wipe everything dry and drive the car and recheck after a couple of days.
Good luck.
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