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Another thing about un-wound Nylguts is that the diameter shrinks as tension is added. If your nut and pip are not smooth they will shave off some of the string. A trick I have tried is to put a piece of cellophane or string package plastic under the strings where they lay in the nut, bring the strings up to tension with that plastic in-between, wait 24 hours, take it out and tension again. The difference in diameter between a new, slack Nylgut and a stretched Nylgut is several thousandths. That's enough to cause a pinch and a break.