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Sounds like the shoulder is being pushed back to far and allowing the case to go to far forward and the extractor can't grab it. Head spacing is off of the shoulder so if you have a max or excessive headspace chamber and min spec die it will push the shoulder back. Try backing out the die 4 turns or so and work in from there to find where it starts to have issues. If this is what's causing it you will most likely have case head separation after a few loading if you full length resize and keep pushing the shoulder back.