A stunning individual display from captain Aaron Smith wasn't enough for the Highlanders, falling to a 21-20 Super Rugby Pacific defeat to NSW Waratahs in Sydney.
Returning after the death of his father last week, Smith looked to have had the decisive say, scoring the try that gave the Highlanders a vital 20-14 lead at Allianz Stadium.
But in the final minutes, a last-gasp try to replacement hooker Mahe Vailanu, and conversion from first-five Ben Donaldson saw the Waratahs sneak in front by a solitary point, and held on to record a victory that keeps them in playoff contention.
The Highlanders meanwhile will go back to the drawing board, suffering their third straight loss, and second consecutive defeat away in Australia.
Defeat leaves the Highlanders eighth on the Super Rugby Pacific ladder, but could mathematically be overtaken by any of Western Force, Queensland Reds or Fijian Drua, depending on results to come this weekend.
After a slow start to proceedings in Sydney, the Waratahs opened the scoring in front of their home fans, as centre Izaia Perese held off multiple defenders to barge his way over for the first try of the night.
And while the Highlanders closed the scores back to 7-6, the Waratahs extended their lead with the final play of the first half.
Thanks to a masterful 50-22 from flanker Michael Hooper, second-five Lalakai Foketi left the Highlanders with no answers, as he went over from close range to give the Waratahs a 14-6 lead at the break.
But, whatever coach Clarke Dermody said at halftime appeared to have worked for the Highlanders.
Right before the hour mark, the Highlanders forwards closed the gap to a point, as Hugh Renton touched down from a rolling maul.
Playing after missing last week's loss to Western Force, Smith then inspired the Highlanders to take the lead for the first time on the night.
Landing a vital 50-22 himself, Smith was then on hand to score from the resulting lineout, as the Highlanders also benefited from a yellow card to Foketi.
From there, though, the southerners couldn't capitalise on their numerical advantage.
The Highlanders didn't score another point in the second-half, and couldn't put the game to bed before Vailanu's decisive try to snatch victory.
The Highlanders are now winless since the end of March, and have their work cut out for them, with a clash against the table-topping Chiefs awaiting them next week in Dunedin.
Highlanders 20 (Renton, Smith tries; Gilbert 2 conversion; Gilbert 2 penalties)
NSW Waratahs 21 (Perese, Foketi, Vailanu tries; Donaldson 3 conversions)