I have never tried it, and have not had much trouble with my sail either. I was just thinking this through, and I think it is a bad idea. once down the sail would not go back up (you might jiggle the ring loose but maybe not and that was the problem you started with) the only emergency I can think of is a violent storm coming in fast and you want to drop the sail, however a gentle capsize might work too or just pulling every flattening string on the boat. So I would learn to wiggle jiggle and finesse your ring to get your sail down. I would hate to be in the ocean with a sail on the deck and no way to hoist it back up. (without capsizing the boat)