I don't have self-tailers and frequently encounter this problem on tacks: I throw two or three wraps on the winch and pull the sheet in rapidly hand-over-hand; the sheet "walks" its way down the winch drum such that the angle from the fair lead causes the sheet to cross over itself on the drum and jam. I then have to take the turns off the winch counter-clockwise to clear the jam, quite difficult if the sheet is under tension. Annoying, and I have missed stays quite a few times due to luffing up to relieve the tension on the sheet to unjam it.
I tried to illustrate in the accompanying drawing - black shows the proper wrap with the tail coming off on top and the sheet from the fairlead coming in on the bottom; red shows the sheet wrapped over the tail.
How can I avoid doing this?

I tried to illustrate in the accompanying drawing - black shows the proper wrap with the tail coming off on top and the sheet from the fairlead coming in on the bottom; red shows the sheet wrapped over the tail.
How can I avoid doing this?

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