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I've sailed a few in-mast boats - I think saying "head upwind when reefing" is too simplistic. Ideally, try to get the sail angle inline with the slot that the sail enters into the mast. If at all possible, don't have it dragging on the lip. The only tension is the outhaul, balanced against your grinding it in.

Of course, this is ideal conditions, but it seems to help the sail wrap with less resistance. If you know what good looks like in good conditions, it hopefully will make you more aware when you have lots of other things going on.

My .02 cents - have fun.

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