my extractor needed some help for the last bit
I'm going to assume you got the FP cover plate off, found the FP/spring, and are trying to get the .22tcm extractor OUT, correct me if I'm wrong
At that point, I had to hook on to the rear of the extractor and pull gently while pushing the claw towards the hole in the breechface gently. (I think I used a dental pick for the pull and one of the 1-3" pieces of bamboo chopstick for the push)
I think it is a symptom of not being a .45 - the breechface is a lot more crowded on a 9mm, so the extractor cutout isn't as wide, maybe?
Installing the 9x19 extractor needed a little fiddling as well.
Oh, a tip for anyone worried about confusing the extractors - I used a piece of copper to scribe "9" and "22" on the rear of the extractors ... it could be done with a soft piece of brass as well (like a .22LR casing)
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I shoot the 9x19 barrel a LOT more than the .22tcm barrel, for obvious cost reasons ... the .22tcm kit is neatly wrapped up and deposited in the plastic box from some CCI mini-mags, it was the perfect size&shape to slip in the safe