Bad extractor or bad ammo?

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Originally Posted by Ron Wood

The extractor is the proper type for a M1900. It is a spring itself, so there is no additional spring under it. It used to be very difficult to find replacements for them, but now some good quality reproductions are being produced. I doubt your extractor needs replaced (at least until it breaks, which hopefully won't happen ).
From your photos, it looks like your extraction problems may stem from the chamber. It looks pretty nasty with lots of pitting. A gunsmith may be able to polish it up a bit, but if that doesn't work, I would think the only alternatives would be a barrel reline or another replacement.

Thanks but I'm almost certain it's not an extractor issue.
Even with a weapon tool (Car key lol) it's difficult to pry the spent casing out of the chamber.

Any extractor would have issues removing the shell with that friction.

I'll have to find an experienced luger gunsmith.

Know one of those?