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Running

Sailing the boat within roughly 30 degrees either side of dead downwind is called a run. This can be the most comfortable point of sail, but requires constant attention. When the wind is coming directly behind the boat, the sailor must sail "wing on wing," one sail on port the other on starboard. Loss of attention by the helmsperson can lead to an accidental jibe, causing injury to the boat or crew. All on deck must be aware of, and if possible avoid, the potential arc of the boom, mainsheet and other gear in case an accidental jibe occurs during a run. A preventer can be rigged to reduce danger and damage from accidental jibes.

Running wing and wing
This is generally the most unstable point of sail, but the easiest for a novice to grasp conceptually, making it a common downfall for beginners. In stronger winds, rolling increases as there is less rolling resistance provided by the sails, as they are eased out. Also, having the sails and boom(s) perpendicular to the boat throws weight and some wind force to that side, making the boat harder to balance. In smaller boats, death rolls can build up and lead to capsize.
Also on a run an inexperienced or inattentive sailor can easily misjudge the real wind strength since the boat speed subtracts directly from the true wind speed and makes the apparent wind less. In addition sea conditions can also falsely seem milder than they are as the waves ahead are being viewed from behind making white caps less apparent. When changing course from this point of sail to a reach or a beat, a sailboat that seemed under control can instantly become over-canvassed and in danger. Any boat over-canvassed on a run can round up, heel excessively and stop suddenly in the water. This is called broaching and it can lead to capsize, possible crew injury and loss of crew into the water.
Options for maneuvering are also reduced. On other points of sail, it is easy to stop or slow the boat by heading into the wind; there may be no such easy way out when running, especially in close quarters or when a spinnaker (including an Asymmetrical spinnaker), whisker pole or preventer are set.