The Sydney to Hobart fleet is bracing for a rough night at sea after the reigning handicap winner, Alive, became the first major boat to quit the race rather than brave the conditions with engine issues.

The Tasmanian 66-footer was one of two boats to withdraw in the first five-and-a-half hours of racing on Boxing Day, as father-son two-hander Transcendence Rudy Project was dismasted and retired north-east of Kiama.

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