Perpetual Loyal again won the battle to be first through Sydney Heads but all four supermaxis experienced issues in one of the most dramatic Sydney to Hobart starts.
With confident talk of weather conditions setting up for a line honours race record, the start on Sydney Harbour was hotly contested.
Eight-time line honours winner Wild Oats XI missed the start badly and had to play catch up while CQS struggled and tilted perilously inside the first five minutes.
Perpetual LOYAL and Scallywag had sail issues close to the first mark.
Within two hours of the start, Wild Oats XI had forced her way to the front and the race had registered it's first retirement, 71-year-old boat Freyja.
It was Anthony Bells' Perpetual LOYAL who made the sweetest start after 89-year- old race icon Syd Fischer fired the starting cannon under northerly breezes of up to 20 knots.
Bell's boat was also first through the heads in last year's race and will be hoping for better fortune this time, having ultimately been forced to retire from that 2015 event, as it had the previous year.
Wild Oats XI skipper Mark Richards was caught swearing on the Channel Seven live coverage amid what he freely admitted was "a terrible start".
Pinned on one side of the course, he had to tack back and thread the needle through a cluster of smaller boats which got the jump on his bigger yacht.
CQS, Ludde Ingvall's radical 100-foot boat, had problems after appearing to suffer a keel issue and lost considerable ground as she tilted steeply to one side.
Following Perpetual LOYAL through the heads was the 80-foot Beau Geste, then Scallywag and Wild Oats XI.
However Wild Oats XI had moved into third by the first mark and went on to reel in the leaders as the fleet headed south down the NSW coast.
The four supermaxis can expect to sail mostly in favourable northerlies, though there is one southerly change forecast around 12 hours in.
"The record will get broken," Scallywag skipper David Witt told AAP.
"Our routing has got one day 11 hours to the Iron Pot, that's seven hours inside the record and with about 12 miles to sail."
Wild Oats XI set the existing record of one day 18 hours 23 minutes 12 seconds in 2012.
"I think it does look optimistic for a race record," Wild Oats XI tactician Iain Murray said.
"The breeze is kind, there's a lot of northerly quadrant wind.
"The race record is not actually that fast, it's 17 knots average or something like that.
"We averaged 21 knots in the Brisbane to Keppel race earlier in the year.
"In a couple of knots of current, there's plenty of opportunity for these 100 footers to go faster than the race record."
The fleet was reduced from 89 after Enigma withdrew a few hours before the start due to engine issues.
The number was reduced to 87 within the first two hours of the race.
The 1945-built 11-metre Freyja from Newcastle, NSW retired, with the cause not immediately clear.
Simplesail Mahligai, an Australian-based boat which is representing Russia in the race, was last out of the heads.
She broke a sail batten but opted to carry on.
Charlotte protested against Triton, but there was no immediate further details.