Sounds like an extractor issue, either that or the rims on the cases are worn out. Here’s my logic….
On a Remington bolt, the extractor is usually stronger than the bolt handle- as in, if the case was really stuck you’d pull the bolt handle off before the extractor gave out. I doubt it’s an extraction timing issue, because the bolt would still be holding onto the case in the chamber, and the whole thing would be locked up.
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