A series of late mistakes cost the Crusaders dearly as they crashed to a 43-40 loss to the Waratahs in Sydney - their sixth defeat of the Super Rugby Pacific season.
Replacement Waratahs first five-eighth Will Harrison delivered the dagger to the visitors, landing a penalty after the hooter had sounded in normal time to level the scores 40-40 before his drop goal sealed victory in the fourth minute of extra time.
It leaves the defending champion Crusaders languishing in second-last place on the standings, having lost their first five matches before seemingly turning the corner by upsetting the Chiefs in their last start.
However, another defeat mounts more pressure on coach Rob Penney and provides some relief for the team he previously coached - the Waratahs - who also went into the match with just one win to their name.
The lead changed 13 times in the nine-try contest but the Crusaders only have themselves to blame they didn't emerge on top.
Reserve flanker Christian Lio-Willie looked to have sealed victory when he crashed over off the blindside of a scrum with 90 seconds remaining to put his side a point in front.
Replacement first-five Rivez Reihana could have wasted the remainder of the clock in taking his sideline conversion, which would have left no time to restart play.
However, he took his successful kick just before the 80th minute mark ticked over, giving the Waratahs one last chance.
From that play, Crusaders winger Johnny McNicholl was ruled to have deliberately knocked on during a Waratahs attack and was shown a yellow card.
Harrison duly slotted the equalising penalty kick and was the hero again in extra time as the Waratahs made it two-from-two in matches against the Crusaders this season.
Penney said his players had learned a harsh lesson about finishing off games.
"Yeah there's some things you can only learn by going through them," he told Stan Sport.
"People have to learn by being exposed and it was a different situation tonight.
"You have your discussions around what it looks like when you're in situations like extra time but it's really living that moment when reality hits."
The early signs had been promising for the Crusaders, with winger Sevu Reece crossing twice in the first 10 minutes.
The second try saw Reece equal Caleb Ralph's record of 52 competition tries for the Crusaders.
The Waratahs worked their way back into the contest, having the edge on the Crusaders at the set pieces and scoring two of their four tries from lineout drives.
Moana Pasifika win
Earlier, Moana Pasifika ensured they will have their best-ever season after beating the ill-disciplined Reds 17-14 in Whangārei.
The visitors had two players shown red cards in the second half, which proved costly as Moana crossed for the match-winning try to first five-eighth William Havili with a minute remaining.
Moana's third win of the campaign means they will eclipse their only two previous campaigns - having won twice on debut in 2022 and just once last year, securing the wooden spoon on both occasions.
They dominated the first half, with Julian Savea's try helping build a 10-0 lead at the interval.
The Reds were vastly improved after the break but paid heavily for the red cards to two of their most experienced players - firstly to halfback Tate McDermott for a swinging arm tackle in the 46th minute and then to flanker Fraser McReight for high contact with seven minutes remaining.