LawConnect has led the Sydney to Hobart fleet out of the Sydney Heads as the 80th running of the bluewater classic gets under way on Boxing Day.
LawConnect's pursuit of a third straight line honours title started on song, with the crew claiming an early lead over rival Master Lock Comanche in second place.
American 88-footer Lucky and Palm Beach XI were in hot pursuit of the defending champions, who have legendary swimmer Ian Thorpe on board this year.
It was the most overcast start to the iconic race in recent years, with boats flying spinnakers from the starting gun to make the best of windy conditions.
LawConnect cruised out of the heads at around 1.10pm AEDT and maintained her lead over Comanche as the fleet began its passage down the NSW Coast.
Earlier, Yendys reported a broken backstay, a vital piece of rigging that runs from the top of the mast to the stern, and was unable to make it to the starting line.
It was a bitter blow for the crew aboard the 55-footer, who had taken former owner Geoff Ross out for a sail in recent days ahead of her first Hobart since 2014.
Yendys suffered the issue just 10 minutes before the start and was seen at port around 2pm as her competitors began making their way down the NSW Coast.
Her retirement reduced the fleet to 128 yachts.
First-time entrant Sumatra suffered hydraulic issues soon after the start and temporarily suspended racing in an attempt to fix the issue inside the Heads, planning to continue racing.
Before the start, the skipper of the Hobart's reigning overall winner warned the fleet to brace for retirements and injuries on the first night of racing.
Friday's final weather briefing confirmed the fleet would face a strong southerly going down the NSW Coast that was set to persist overnight.
Crews can expect a cold first night and swells between three and four metres, with upwind conditions also increasing the chance of damage to boats.
Conditions are unlikely to be as treacherous as last year, when two sailors were killed in storms, but the fleet is nevertheless on guard.
"I think there will be retirements, it's tough on boats in the early part of this race," said Celestial V70 skipper Sam Haynes, who is also Commodore of the Cruising Yacht Club of Australia.
"The crash bang, the waves, the gear itself is going to be under stress so it is a hard race in that sense.
"Also it's hard on crews: seasickness and potentially some injuries. They can put boats out. I think there will be some retirements in these conditions."
Conditions are expected to become lighter on Sunday as the fleet's 100ft supermaxis approach the finish line at Constitution Dock.
LawConnect is heavier than Comanche, enjoys rough conditions and boasts an impressive crew, all of which should play into her hands in the fight for line honours.
But on Friday morning, owner Christian Beck again downplayed his boat's chances of a third consecutive triumph.
"It's a bit like (F1 driver) Max Verstappen likes it when it's raining, we like it when it's very rough," he said.
"This forecast is a little bit rough but it's probably not rough enough to make it that likely that we'll win, unfortunately."
The fleet paid tribute to the victims of the Bondi terror attack by scattering rose petals off the coast of Bondi Beach as they passed early in the race.
At the final briefing, extra rose petals were made available, with the whole fleet expected to participate.
