Sydney to Hobart leader Master Lock Comanche is keeping a "close eye" on major rival LawConnect as the two supermaxi yachts fight out a tight tussle for line honours.
Comanche held a narrow advantage of four nautical miles over LawConnect, which is aiming for a third straight first-past-the-post win, in Bass Strait at 5.30pm on Saturday.
The retirement list grew further on the second day of sailing, with one of the favourites for the handicap crown, URM Group, forced to pull the pin with hull damage about 4.30pm.
It is the second time in as many years the 72-footer has retired after it was dismasted in 2024 and had to motor seven hours back to safety for repairs.
URM Group reported all crew were OK and the boat was making a six-hour trip to the NSW south coast.
The overall retirement tally sat at 15 by Saturday evening, including supermaxi Wild Thing 100, which suffered rigging issues off the NSW south coast in the early hours of the morning.
Crews have battled uncomfortable and seasickness-inducing upwind conditions, which are expected to ease into Sunday.
Andy Green, navigator for Comanche, which is seeking redemption after being forced to retire with mainsail damage in 2024, said he was expecting winds to lighten closer to Tasmania.
LawConnect was first out of Sydney Heads on Boxing Day, but surrendered her lead after tacking out to sea after 6pm on Friday.
"We're keeping a good close eye on them and a nice cover on any radical strategy they might do to try and force a decision on us," Green said.
LawConnect, skippered by Christian Beck, was forced to contend with a broken mainsheet and halyard on the first night.
"It's been a tough night, we had a lot of breakages," he told AAP.
"It's been quite difficult. We're still together, we're still in the race."
LawConnect crew member Chris Nicholson said it had been "a bit of a horror show" after the yacht lost its wind instruments at the beginning of the event.
"(We were) looking forward to daylight so we could see the sails again," he said.
An afternoon line-honours finish on Sunday is on the cards, well behind last year's 2.35am arrival and the race record of one day, nine hours, 15 minutes and 24 seconds set in 2017.
Supermaxi SHK Scallywag and American 88-footer Lucky were in second and third, with NSW's Palm Beach XI a touch further back in a remaining fleet of 113.
Wild Thing's withdrawal was gutting for veteran skipper Grant Wharington, who oversaw significant upgrades to her this year.
Wild Thing was third on line honours in the deadly 2024 Sydney to 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," Wharington said.
"We got that fixed but we just weren't happy with the set-up. 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."
The fleet sailed upwind in winds of 25 knots on the first night with seas of 2-3 metres.
"It's really uncomfortable and tough on the body with confused big seas," said Jo Clarke, crew member aboard cruiser Rum Bucket.
"Lots of seasickness, but people are starting to recover."
Troubadour and Roaring Forty retired because of crew members suffering seasickness, while Moneypenny stopped racing after losing a life raft and failing to comply with requirement.
The Bureau of Meteorology expects the wind to shift direction into Sunday and give the fleet some help down Tasmania's east coast.
