Oversize oil drain plugs

[360CJ]

When I got my engine, the oil drain plug was stripped with some toggle bolt gasket thing there. I got a 1/2 size oversize plug and put that in. It worked but then stripped out too. I picked up a 1 size oversize plug but I can't get it to cut a thread. So far I've managed to just strip the cutting threads on the end of the plug. Anyone got a tip on geting one of these started? I doubt I could find the right size tap for this.

[Warlock]

Hate to say this, but look for a tap, and cut new threads. Then put a normal drain bolt in.
OS bolts are really only intended for one use. I know I have used a few a couple of times (customers are too cheap to get drain pans tapped), but never with good results. They always end up leaking.

[360CJ]

Ok. Since it was a 1/2" plug, what size should I tap to? 9/16"? I was holding back on buying a tap to see if anyone had a cheaper idea.

[Warlock]

9/16 would work as it is the next size up (without going metric). But unfortunately it is probably the best you are going to be able to do without pulling the pan.