Scotland slipped to a third successive Six Nations defeat as they fell to a battling Italian side at Murrayfield.
Mark Bennett ran in his first international try for the Scots before Joshua Furno and Giovambattista Venditti replied for Italy.
Greig Laidlaw’s 14 points with the boot kept them in front until the final minute.
But Vern Cotter’s side were undone by a last-gasp penalty try, which was converted by Tommaso Allan.
The result leaves Scotland bottom of the Six Nations table as the only team without a victory to their name while Italy secure their first championship win since 2013.
Scotland’s performances in defeats by France and Wales had offered some signs of encouragement, but there will be no crumbs of comfort in losing to Italy, who celebrate a first win in Edinburgh since 2007.
With matches against title contenders England and Ireland to come, the Scots are staring at the very real prospect of a Six Nations whitewash.
They started the match in positive fashion. Captain Laidlaw kicked Scotland in front with barely a minute on the clock after an Italian infringement, and it was immediately obvious the Scots were aiming to play a more expansive game than in those opening two matches.
The Scots’ ambition was helped by some sloppy Italian play, fly-half Kelly Haimona’s wayward pass an open invitation for Mark Bennett to intercept and coast under the posts unchallenged.
The visitors were not about to crumble though. A driving maul from a line-out on the Scotland 22 carried the Italians over the try line, with lock Furno the man grounding.
Two Laidlaw penalties either side of Haimona’s three-pointer extended Scotland’s lead to 16-8, but they conceded just before half-time through a slice of bad fortune.
Haimona’s penalty attempt came back off the post and the ball bounced favourably to wing Venditti, who managed to force the ball down through a ruck of bodies to make it 16-15 at the break.
Scots-born fly-half Allan, on for Haimona, spurned a good chance to put Italy in front for the first time on 54 minutes, sending a fairly straightforward penalty attempt wide of the posts.
For the second match running the home side had a try ruled out, though in this instance there was no controversy; Sean Lamont’s off-load to Stuart a blatant forward pass.
Laidlaw nudged Cotter’s men four points ahead with a routine penalty 13 minutes from time, but the Italians would not lie down.
They forced a succession of line-outs and scrums deep in Scottish territory, and with the home defence desperately trying to halt a rolling maul, referee George Clancy deemed they were doing so illegally and awarded a match-winning penalty try, which was converted by Allan to seal a desperately disappointing day for the Scots.
Hogg, Seymour, Bennett, Dunbar, Lamont, Horne, Laidlaw, Dickinson, Ford, Murray, Swinson, Gray, Harley, Cowan, Beattie.
Scott for Bennett (67), Tonks for Horne (80), Hidalgo-Clyne for Laidlaw (78), Grant for Dickinson (68), Brown for Ford (67), Cross for Murray (78), Toolis for Swinson (70), Watson for Beattie (51). Sin Bin: Toolis (79), Watson (80).
McLean, Visentin, Morisi, Bacchin, Venditti, Haimona, Gori, Aguero, Ghiraldini, Chistolini, Biagi, Furno, Minto, Favaro, Parisse.
Bisegni for Visentin (70), Allan for Haimona (44), De Marchi for Aguero (58), Manici for Ghiraldini (71), Cittadini for Chistolini (58), Fuser for Biagi (69), Vunisa for Favaro (62). Not Used: Palazzani.
George Clancy (Ireland).