1/2-20 Time-sert sleeve for oil pan drain ?

Maybe it might have to be. That's why I was banging my head. To do a good job the pan once reinstalled will have to sit overnight na dbe retightened.
I use O-A and that is extra difficult in corners, never mind inside a 'box'.
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Another option is to use the pan shown above, although it had a rust hole the machine shop brazed from the outside. So the pan's lifespan may be somewhat limited...

This pan (shown below) had no deep pitting, just hte compromised drain plug. :(
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Maybe a local college or fab shop could tig it for you. Sucks there’s not really a simple solution here.