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From a winch. lol or more of a chuckle instead

If the line isn't tight on the drum in the first few layers it's soft and will let the outer wraps, under tension, bury itself in the soft layers causing the binding you are talking about. So if you can watch it respooling and try and make the bottom layers nice and neat. If you go on Samsons...

Respool the line with some weight on the end it sounds like the line is burying itself in a loose winding. I hope that made sense.