Had the exact same problem on a Remington Model 7 that some fuckwit 'gunsmith' put a PTG Rem 700 bolt into and never bothered to check headspace.
I'd put £20 on it being long-chambered, the brass is expanding too much and what you are seeing is the result of trying to rip a piece of brass out of the chamber which has not been able to spring back enough. Being able to lift the bolt up to the primary extraction cam is a good sign, as that is often done wrong in a re-barreled Remington to where the primary extraction surfaces on the receiver and bolt handle miss each other entirely.
Borrow a No-Go gauge (or if you can only find a Go gauge, put a single layer of masking tape on the case head) and I bet the bolt will still close. This is quite an unsafe condition as you are stretching the brass beyond it's elastic limit. If you want to verify this, go find or buy an L.E Wilson case gauge ( https://lewilson.com/case-gage ) and I bet your brass will protrude from the rear end of it. Another thing to confirm this hypothesis is find another person with a 300WSM who reloads, get them to run your case through their FL sizing die and try and chamber it. It probably won't chamber and will require a small base die to get it sized down around the case web (you are better off binning all the fired brass at this stage TBH)...
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