The Sydney to Hobart fleet is bracing for a rough night at sea with reigning handicap winner Alive the first boat to retire from the iconic race rather than face the difficult conditions.
Line honours favourite Master Lock Comanche led the fleet into the night after overtaking incumbent LawConnect, which experienced a furling issue coming out of Sydney Harbour in a crisp north-easterly.
LawConnect's furling problem has since been fixed, but allowed Comanche to open up a gap that grew beyond 8nm in the afternoon.
LawConnect closed to just more than 5nm as the fleet approached Eden on NSW's south coast around 10pm after the two line honours front-runners came in towards the shoreline.
Fellow supermaxis Wild Thing 100 was in third place by that point, around 14nm behind LawConnect and ahead of mini-maxis Celestial V70 and URM Group.
A west south-westerly change is expected to hit the Bass Strait overnight, bringing winds up to 40 knots and possible showers - conditions that will be particularly challenging for the smaller boats in the fleet.
But even the four 100ft supermaxis risk damage amid the wild weather, which could be race-defining and force more retirements from a fleet standing at 101 yachts.
Tasmanian 66-footer Alive was one of three yachts to withdraw during the first evening of racing on Boxing Day, citing a mechanical issue in her engine.
Duncan Hine's boat retired off Wollongong around 4pm.
Alive had only just returned to the water following last-minute repairs on a damaged canard board that forced her out of this month's Cabbage Tree Island Race and Big Boat Challenge.
The crew felt it would be unsafe to continue with the latest issue given the conditions awaiting in the southern NSW Coast and Bass Strait.
The retirement is a bitter blow for Alive, which was vying to become only the fourth boat in history to win the race on handicap three times, after Freya, Love & War and Ichi Ban.
Instead of forging ahead, Alive buoyed at Port Kembla for engine repairs as fellow handicap contenders URM Group, Celestial V70 and Zeus waged on.
Later, father-son two-hander Transcendence Rudy Project was dismasted and retired north-east of Kiama just before 6:30pm, steering issues then forcing Ciao Bella to withdraw after 8pm.
The fast start will have been a big confidence booster for Comanche after LawConnect ambushed her in the River Derwent to take line honours by only 51 seconds last year.
The 2023 race was front of mind for Comanche's two new co-skippers before they set out on Boxing Day.
"We've got one goal, we're going to lock this up," James Mayo said.
"There's a lot of people who sailed on this boat last year who missed out narrowly and this year, they're hungrier than ever."
Drama unfolded early on as fellow supermaxi Wild Thing 100 narrowly avoided a collision with Celestial V70 before recapturing her speed out of the Heads.
Wild Thing was at the centre of another incident in the harbour that left leading URM Group to complete a penalty turn.
URM Group had been required to keep clear of a cluster of boats on her starboard side but struggled to do so with Wild Thing so close leeward.
Just as Whisper flew a protest flag, claiming the mini-maxi had been too close, URM Group completed a penalty turn to absolve herself for the misstep.
Penalty turns for incidents that take place in the harbour must be completed early in the race, or else the offender risks a time penalty on arrival in Hobart.
