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do I just need to loosen the collet and have the pin fall out?
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Yes.
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How easy is it to put back and in the right position?
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Easy, it is a collet...it is self centering. If you are worried about it, leave it loose, put a case that has already been deprimed in the shell holder, and make sure the decapping pin is protruding through the flash hole before you tighten the collet-nut.
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What would be the most likely cause of this?
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The Lee decaping rod/collet needs to be pretty tight to keep it from slipping.