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Throw the Wilson gage away and order a Sinclair ammunition gage with the cut out, drop in a re-sized loaded round and your problem will become very clear. The Wilson is only good for case length in my opinion, the Sinclair is made with a chamber reamer and will show you where the problem lies. You need you measure the head space set back on your resized cases as well. Screwing down the resizing die to better resize the head diameter smaller is also bumping the head space back way too far and your brass is going to suffer a short life. Again trim length is very important too.