Hobbit compression woes & cylinder bolts that won't torque down

Jessie Paull /
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I just finished putting my the top end of my engine back together, and to my dismay my poor Hobbit no longer starts. It seems to be a lack of compression.

I had just had my cylinder off and replaced my piston rings, and when I put it back on I torqued the bolts down to 7ft/lb (manual said between 5.6 and 8.7) Thinking maybe the bolts needed a little more torque, I set my wrench to 8ft/lb and started turning each one down in a star pattern.

3 out of 4 bolts clicked, but the top right bolt just kept going. After a couple cranks I start getting nervous - maybe I'm gun shy bc I just broke a bolt off (other side) a few weeks ago and it was agonizing getting it out - so I pull the bolt out to look at it.

In the attached picture #1 is a spare bolt I had laying around, #2 is the bolt I just took out, and #3 is the second bolt I tried next.

To me bolt #2 looks a little fucked up, like the threads were stretching out and it was about to snap. So I take another spare bolt and start torquing down, but that seems like I've turned my wrench way too many times too and so I take that one out too (#3)

Am I crazy? Should I just trust the torque wrench, or is it possible something is wrong with the hole in the case? I'm wondering if this might be the issue with my compression. (edited)

IMG_20200728_195224~2.jpg
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