Prevent damage by working together to raise the main sail! Often, the person on the winch has a clear view of the sail and should be looking up while they grind to make sure that nothing is getting caught and everything is going up smoothly. What if they are under the dodger or paying attention to other details? Many boats are equipped with dodgers that will obstruct your view of the sail while you are at the winch. Many of the same boats are equipped with Stack Packs, Lazy Jacks, Dutchman, or other sail flaking systems. Be sure that someone is watching the main go up as it is being raised. Often battens will get caught on lazy jack lines and the sail will need to be dropped down a few inches to clear it and re-raised. In the extreme case, the halyard may be hooked up to the head of the sail, but without a clear shot to the top of the mast (It pays to take a good look UP when attaching the halyard as well, to make sure you are clear of spreaders, lazy jacks, and other rigging). As a prepared skipper, be sure you have assigned someone to watch the sail as it is raised and save yourself from broken rigging and lost halyards.
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I recently spent a month crewing on a sailboat with an electric winch for the main halyard and main sheet. When raising the main sail with an electric winch it is even more important to watch the sail as it goes up. With the electric winch you have no idea when it is getting hard to hoist and you can really do a lot of damage. Also, it is good practice to stop using the electric winch before the main sail is all the way up; use the winch handle for the last bit so that you can feel the tension.
An electric winch can also do a lot of damage to a person. See this article.
http://bwsailing.com/cc/2011/03/29/freak-accident-in-antigua-brings-safety-reminders-for-cruisers/