Hi Shel, I think these old flatheads are prone to some oil leaking. This drain plus all of a sudden got to be a bit much, so gave the drain plug a coating of permatex #2, stopped the leaking so far.
I will pull the oil pan and correct, either a swap or send in for repairs.
The oil pan bolt hole seat, where the plug and gasket sit, is somewhat distorted, no wonder it could not seal, the threads could have been a bit tighter too.
So by coating with the permatex, no doubt is stopping the weeping of the oil, at least for a while, or at least a slow down. I see no leaking so far, been about 6 hours.
Undercoatney, certainly would not hurt....Fred
Pic of the extra plug, 1 copper gasket, 1 nylon NAPA gasket, 1 steel, that was on the plug on my engine, the metal gaskets all lok roughed up, the one on my engine had a rubber type surface on it, not sure if someone tried RTV before I got this engine....