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I read your post again and got to the part about denting the rim. The extractor fits into a recess machined into the bolt. If there is enough crap BEHIND the extractor (in the cutout) it may not be allowing the extractor to move out of the way of the rim as the cartridge is chambered. Clean with an old tooth brush really good. With the bolt out of the rifle fit a case under the lip of the extractor and pivot it into the bolt. The extractor should move out of the way a tad allowing the case to seat against the bolt face. Just a thought.
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