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You want the sail right up to the black band, best achieved with everything else freed off completely while you hoist. Whether you take the gooseneck off while you do this is up to you, but it shouldn’t actually be necessary.

The common problem here is that when a mainsail gets a few years old the bolt rope running up the luff shrinks a couple of inches. This makes it very hard to get the sail up to the black band and usually results in having to take the boom off while you get the halyard up, then swing down on it with the weight of several rhinos whilst trying to hook the boom back on the gooseneck and usually trapping your fingers in the process.

If this is the case you will also tend to find that the sail sets badly and the cunningham is a complete waste of time, as all it does is pull the bolt rope without actually tensioning and flattening the sail.

If this sounds familiar then you need to release the bolt rope a bit. Undo the stitching at holding it into the sail at the tack, then with the head of the sail fixed somewhere stretch the luff out until you feel the end of the rope go up the sail by the required amount. Then re-stitch the end of the bolt rope to secure it in the new position.