In looking at the picture, I guess it's half empty or half full, but my impression that there is something wookie with the left extractor. Hard to tell with the camera angles, but it looks to me like it may not be fitting the cutout hardly as well as the right. You never mentioned I don't think, but does it happen in one barrel more than the other?
You mentioned being free once lifted by the extractor. I have seen this both in shotguns and rifles. A small imperfection in the chambe can cause this. When shooting a load of even moderate pressure, the shell can expand just enough to hank in the imperfection. Once pulled loose, it comes on out. When I mentioned lengthening forcing cones or chambers, it is possible for a hand held reamer to do this at the back of the cutter if the alignment is not good enough. Your chamber hasn't been lengthened, but someone may have used a combination reamer to cut a new forcing cone and run it in a lattle too far. If you have a bore gauge, you could carefully measure the chambers from front to back and see if there is a slight constriction toward the back. If you don't have one you may be able to find someone who does or try a gunsmith to measure the chambers.
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