The Sydney to Hobart fleet has lost its first 100ft supermaxi with Wild Thing 100 making the "very disappointing" decision to retire from the 80th running of the race.
All crew were safe as Wild Thing began the journey back to Sydney after 3.30am on December 27, having succumbed to a rigging issue east-north-east of Tuross Head on the NSW South Coast.
Wild Thing had been considered a long shot for line honours compared to overnight leader Master Lock Comanche and reigning champion LawConnect, who were separated by around four nautical miles by 11am AEDT.
At that time, the two heavyweights were into the Bass Strait, though neither will break the race record set by Comanche in 2017 - one day, nine hours, 15 minutes and 24 seconds.
LawConnect was forced to contend with a broken mainsheet and halyard overnight but managed to fix both issues and remain in pursuit of Comanche.
Out for redemption after retiring with mainsail damage last year, Comanche opened up a larger gap on LawConnect as the boats approached Eden.
"It's been a tough night, we had a lot of breakages, which is why Comanche is ahead of us," LawConnect skipper Christian Beck told AAP on Saturday morning.
"It's been quite difficult.
"We're still together, we're still in the race, but we've had a tough night.
"If we didn't have those (mainsheet and halyard) issues, we would have been fine."
Supermaxi SHK Scallywag and American 88-footer Lucky led the chasing pack into the Bass Strait.
Wild Thing's withdrawal was gutting for veteran skipper Grant Wharington, who oversaw significant upgrades to her this year.
Wild Thing had placed third on line honours in last year's deadly Hobart even with a smaller rig than usual for a 100ft supermaxi, and had a larger one installed in May.
"Very disappointing, this morning about 3.30 we were trying to repair a problem with the rudder. We got that fixed but we just weren't happy with the set-up," said Wharington.
"We kept breaking runner tails and had some other rigging issues as well. Conditions were pretty testing and we lost quite a lot of time in trying to fix those problems so we decided it was prudent to pull out.
"It's a tough race, isn't it? It's something that pushes the limits of technology and people's endurance. Unfortunately it wasn't to be our year."
Despite crews being told to brace themselves for rough conditions, Wild Thing was the only boat to retire overnight by 5am after a handful pulled out on the afternoon of Boxing Day.
Awen retired with a broken forestay around 5.30am before engine issues left Trouble & Strife as the sixth boat to pull out about an hour later.
Two further yachts, Troubadour and Roaring Forty, pulled out as crew members suffered seasickness, reducing the fleet to 120 boats.
The fleet sailed upwind in tops of 25 knots overnight with solid swell as predicted.
Conditions were nowhere near as treacherous as last year's first night, when two sailors were killed in violent storms.
Beck was bracing for tough sailing later on Saturday, though.
"It's kind of going to get worse later, we think," he said.
Hutchies Yeah Baby (damaged headstay foil), White Noise (rigging issues) and two-hander Inukshuk (rudder problem) had all retired by 5pm on Boxing Day.
Silver Fern continued racing overnight after initially turning back for some ad hoc repairs, while Yendys scratched before the starting gun with a broken backstay.
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