Sailors wishing to master the Contender must learn how to trapeze and steer the boat at the same time, and how to move about the boat while keeping it level. As part of race tuning, the Contender mast is commonly raked well aft, which results in restricted space between the boom and deck. Tacking consequently requires technique and practice to avoid getting stuck under the boom. Sailing the boat level at all times (except in very light winds) is fastest and reduces capsizes, which can happen fast if the boom dips into the water. There is a trade-off between raking the mast far aft and keeping the kicker tight at all times (which is faster) and the higher probability of capsizing due to this less forgiving set up. Unlike older and heavier dinghy designs, the Contender requires the centerboard to be lowered at least somewhat to avoid quick capsizes when reaching and running in a breeze.