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Here's what I did to fix the problem. A friend of mine who is a diesel mechanic helped me turn the engine by hand. We could see the bottom of the piston skirt come down and when it bottomed out the bottom piston ring (wiper) was right at the hole. We never saw the top of the ring. We measured...

Here is a picture of the freeze plug opening and the 1/8" drill hole.

I appreciate the many comments and suggestions. Here is a little more information that has been requested by posters. The drilled hole is 1/8" diameter. It is on the left side of the engine, the farthest foreward freeze plug hole. I poked a wire through the hole, and it appears the hole is...

I bought an engine block heater that mounts into a freeze plug hole. Someone told me that to get the freeze plug out, I should drill a small hole through the plug and put a screw into the hole to have something to pull on. Well, I did way too good a job drilling the hole. When I got the plug...